[ CAS No. 1072-67-9 ] {[proInfo.proName]}

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Quality Control of [ 1072-67-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1072-67-9 ]

SDS Specification

Alternatived Products of [ 1072-67-9 ]

Product Details of [ 1072-67-9 ]

CAS No. :	1072-67-9	MDL No. :	MFCD00003155
Formula :	C₄H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FKPXGNGUVSHWQQ-UHFFFAOYSA-N
M.W :	98.10	Pubchem ID :	66172
Synonyms :	5-Methyl-1,2-oxazol-3-amine

Calculated chemistry of [ 1072-67-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	25.87
TPSA :	52.05 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.14
Log Po/w (XLOGP3) :	0.13
Log Po/w (WLOGP) :	0.57
Log Po/w (MLOGP) :	-0.27
Log Po/w (SILICOS-IT) :	0.66
Consensus Log Po/w :	0.45

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.06
Solubility :	8.57 mg/ml ; 0.0874 mol/l
Class :	Very soluble
Log S (Ali) :	-0.78
Solubility :	16.3 mg/ml ; 0.166 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.18
Solubility :	6.42 mg/ml ; 0.0655 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.26

Safety of [ 1072-67-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1072-67-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1072-67-9 ]
Downstream synthetic route of [ 1072-67-9 ]

[ 1072-67-9 ] Synthesis Path-Upstream 1~1

1
[ 1072-67-9 ]
[ 121-60-8 ]
[ 21312-10-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	at 20℃; for 12 h;	A mixture of 4-acetamidobenzene-1-sulfonyl chloride (4.27 mmol), 5-methylisoxazol-3-amine (4.49 mmol) and DMAP (0.21 mmol) in anhydrous pyridine (10 mL) was stirred at room temperature for 12 h. After completion of reaction, solvent was evaporated to dryness and diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and 1 M aqueous HCl, dried over anhydrous Na₂SO₄, filtered, and concentrated under vacuum. The solid residue obtained was purified with flash column chromatography using heptanes to EtOAc (50-100percent) gradient elution to afford the compound 2. 4.2.1 N-(4-(N-(5-Methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide (2) Yield: 59percent; ESIMS m/z calcd for C₁₂H₁₃N₃O₄S [M + H]⁺, 296.07; found 296.06; ¹H NMR (400 MHz, (CD₃)₂SO): δ 11.30 (bs, 1H), 10.35 (bs, 1H), 7.79-7.73 (m, 4H), 6.12 (s, 1H), 2.29 (s, 3H), 2.07 (s, 3H). ¹³C (100 MHz, (CD₃)₂SO): δ 170.71, 169.57, 158.07, 144.01, 133.36, 128.50, 119.15, 95.84, 24.57, 12.48.

Reference： [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 1, p. 12 - 17
[2] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 595 - 603
[3] Shionogi Kenkyusho Nenpo, 1957, # 7, p. 301,304[4] Chem.Abstr., 1957, p. 17889
[5] Patent: US2888455, 1957, ,
[6] Crystal Growth and Design, 2013, vol. 13, # 9, p. 4002 - 4016
[7] Patent: CN105884705, 2016, A, . Location in patent: Paragraph 0013; 0016; 0021; 0026; 0031

[ 1072-67-9 ] Synthesis Path-Downstream 1~6

1
[ 1072-67-9 ]
[ 51991-94-7 ]
[ 106695-66-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346

2
[ 1072-67-9 ]
[ 53308-95-5 ]
[ 794564-70-8 ]

Yield	Reaction Conditions	Operation in experiment
		Boc-novaline (2.3 MMOL) was dissolved in 20 mL of anhydrous dichloromethane under N2 at rt. Diisopropylethylamine (6.9 MMOL) was added, followed by TBTU (2.8 MMOL). The reaction mixture was stirred for 10 minutes. The ISOXAZOLE R was then added and the reaction was stirred for an additional 16 h. The crude material was diluted with 50 mL of EtOAc and washed with 50 mL portions of water and then aqueous saturated sodium chloride solution. The organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The products were isolated through flash chromatography on silica gel to yield the desired intermeidates (Table 1).

Reference： [1]Patent: WO2004/99200,2004,A1 .Location in patent: Page 33-34

3
[ 1072-67-9 ]
[ 3044-06-2 ]
[ 1228657-25-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol; for 36h;Reflux;	General procedure: An ethanol (20 ml) solution of 3-amino-5-methylisoxazole 1 (5 mmol) and diethyl ethoxymethylenemalonate 2a-d (5 mmol) or ethoxymethylenecyanoacetate (5 mmol) 2e-h was heated under reflux, until the reaction was completed. The solvent was then removed under reduced pressure, and the residue was washed with ether. The enamines 3a-d were purified by column chromatography over silica gel (eluant: AcOEt/Cyclohexane:1/5) and the enamines 3e-h were recrystallized from hexane.

Reference： [1]South African Journal of Chemistry,2010,vol. 63,p. 62 - 64
[2]Revue Roumaine de Chimie,2012,vol. 57,p. 901 - 906

4
[ 1072-67-9 ]
[ 3044-06-2 ]
[ 1228657-28-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	In 5,5-dimethyl-1,3-cyclohexadiene; for 48h;Reflux;	General procedure: To a solution of 3-amino-5-methylisoxazole 1 (5 mmol) in xylene (15 ml), ethoxymethylenemalonate 2a-d (5 mmol) was added and refluxed for 48 h. The solvent was removed and the residue was purified by column chromatography over silica gel (eluant: AcOEt/Cyclohexane:1/3) to yield isoxazolo[2,3-a]pyrimidinones 4a-d.

Reference： [1]Revue Roumaine de Chimie,2012,vol. 57,p. 901 - 906

5
[ 1072-67-9 ]
[ 3621-82-7 ]
6-chloro-N-(5-methylisoxazol-3-yl)benzo[d]oxazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%		To a solution of 5-methylisoxazol-3-amine (300mg, 3.O6mmol) in dry THF (lOmL) was added sodium hydride (60percent in mineral oil, 366mg, 9.l7mmol) at 0 00. The resulting mixture was stirred at 0 00 for 15 mm and 2,6-Dichlorobenzo[d]oxazole (575mg, 3.O6mmol) was added. The reaction mixture was further stirred at rt for 16 h. TLC showed the reaction to be complete. The reaction mixture was quenched with sat. aq. NH4CI solution (2OmL) and extracted with EtOAc (3x2OmL). The organic layer was washed with brine (2OmL), dried (Na2SO4), filtered and concentrated under reduce pressure. The residue was triturated with Et20 (25mL) and dried under vacuum to give N-cyclopropyl-2-((5-(trifluoromethyl) benzo[d]oxazol2-yl)amino)thiazole-4-carboxamide as a yellow solid. Yield: 99mg (13percent); MS (ESl+) for CHNOS m/z 249.99 [M+H] LC purity 99.8percent (Ret. Time = 5.96mm); 1H NMR (400 MHz, DMSO-d6 + D20): 7.60 (5, 1H), 7.39 (d, J= 7.5 Hz, 1H), 7.25 (d, J= 7.5 Hz, 1H), 6.62 (5, 1H), 2.35 (5, 3H).

Reference： [1]Patent: WO2018/37223,2018,A1 .Location in patent: Page/Page column 197; 198

6
[ 1072-67-9 ]
[ 117-21-5 ]
4-chloro-2-(5-methylisoxazol-3-yl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With acetic acid; at 110℃; for 4h;	General procedure: The starting materials 1 and 2 were commercially available (Energy Chemical, Shanghai, China).Compound 2 (3.72 mmol) was added to a stirred solution of compound 1 (3.38 mmol) in glacial aceticacid (10 mL). The reaction mixture was then stirred at 110 C for 4 h. After completion of the reaction,the solvent was evaporated, and the residue was purified on a silica gel column chromatography andeluted with ethyl acetate/petroleum ether (bp 60-90 C) (1:3, v/v) to give compounds 3.

Reference： [1]Molecules,2019,vol. 24

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Isomers

Technical Information

? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Hydride Reductions ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Amines ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction

Historical Records

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[ 1072-67-9 ]

Amines

[ 19754-80-4 ]

5-Ethylisoxazol-3-amine

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3-Amino-4,5-dimethylisoxazole

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3-Amino-5-tert-butylisoxazole

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[ 1750-42-1 ]

Isoxazol-3-amine

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[ 440099-32-1 ]

Isoxazol-5-ylmethanamine hydrochloride

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Related Parent Nucleus of
[ 1072-67-9 ]

Isoxazoles

[ 19754-80-4 ]

5-Ethylisoxazol-3-amine

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[ 13999-39-8 ]

3-Amino-4,5-dimethylisoxazole

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[ 55809-36-4 ]

3-Amino-5-tert-butylisoxazole

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[ 1750-42-1 ]

Isoxazol-3-amine

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[ 5765-44-6 ]

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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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[ CAS No. 1072-67-9 ] {[proInfo.proName]}

Quality Control of [ 1072-67-9 ]

Related Doc. of [ 1072-67-9 ]

Product Details of [ 1072-67-9 ]

Calculated chemistry of [ 1072-67-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1072-67-9 ]

Application In Synthesis of [ 1072-67-9 ]

[ 1072-67-9 ] Synthesis Path-Upstream 1~1

[ 1072-67-9 ] Synthesis Path-Downstream 1~6

Technical Information

Related Functional Groups of [ 1072-67-9 ]

Amines

Related Parent Nucleus of [ 1072-67-9 ]

Isoxazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1072-67-9 ]

Related Parent Nucleus of
[ 1072-67-9 ]