Methylamine → HCID 67464618, compound

HRID 469731Notes

Reaction equation

[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][C:15](=[O:18])[N:14]2[C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22](O)=[O:23])=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ClCCl.[CH3:31][NH2:32]>>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][C:15](=[O:18])[N:14]2[C:19]2[CH:27]=[CH:26][CH:25]=[C:21]([C:22](=[O:23])[NH:32][CH3:31])[CH:20]=2)=[O:12])[CH:6]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

Reactant 3

HCID 6329Methylamine

HCID 6344Dichloromethane

HCID 67460966HCID 67460966, compound

Product 1

HCID 67464618HCID 67464618, compound

Procedure

To a stirred solution of 3-[(S)-2-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-5-oxo-pyrrolidin-1-yl]-benzoic acid (75 mg, 0.2 mmol) in dichloromethane (1 mL) 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC hydrochloride) (42 mg, 0.22 mmol) is added at room temperature. After 5 minutes methylamine (0.5 mL of 2 M solution in tetrahydrofuran, 1 mmol) is added. After 2 h solvent is removed in vacuo and the crude is purified by chromatography over silica gel eluting with methanol/dichloromethane to give the title compound as a white solid, ESI m/z 385 [M+H]+.

Workup

customAfter 2 h solvent is removed in vacuo
customthe crude is purified by chromatography over silica gel eluting with methanol/dichloromethane

Sources & evidence

ORD record: ord-698c79589b0044eda6cc156dcbf016c7
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629157B2

Reaction notes

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