Triethylamine → (S)-5-(4-Chlorophenyl)-4-methyl-N-(tetrahydrofuran-3-yl)isoxazole-3-carboxamide

HRID 1510432Notes

Reaction equation

HRID 1510432 reaction equation
[O:1]1[CH2:5][CH2:4][C@H:3]([NH2:6])[CH2:2]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19](O)=[O:20])[C:15]=2[CH3:22])=[CH:10][CH:9]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>O1CCCC1.CN(C)C=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]([NH:6][C@H:3]3[CH2:4][CH2:5][O:1][CH2:2]3)=[O:20])[C:15]=2[CH3:22])=[CH:12][CH:13]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 14243168(S)-3-AminotetrahydrofuranHCID 671210815-(4-Chlorophenyl)-4-methylisoxazole-3-carboxylic acid

Product 1

HCID 67121092(S)-5-(4-Chlorophenyl)-4-methyl-N-(tetrahydrofuran-3-yl)isoxazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-Tetrahydrofuran-3-amine (13 μL, 0.13 mmol) was added to a mixture of 5-(4-chlorophenyl)-4-methylisoxazole-3-carboxylic acid (23 mg, 0.10 mmol), 1-hydroxybenzotriazole hydrate (16 mg, 0.12 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (22 mg, 0.12 mmol) and triethylamine (16 μL, 0.12 mmol) in tetrahydrofuran (0.8 mL) and N,N-dimethylformamide (0.1 mL). After stirring overnight, the volatiles were removed in vacuo and the compound was purified by silica gel chromatography eluting with 2% methanol in dichloromethane to afford the title compound: (21.6 mg, 0.07 mmol). MS (ESI) m/z (M+H+): 307.0.

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe compound was purified by silica gel chromatography
  3. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-9ba54b7055f1448dbc82076bdb01b008
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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