Pyrrolidine → HCID 70864987, compound

HRID 336195Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([C:10]1[O:14][N:13]=[C:12]([NH:15][C:16]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:24](=[O:27])[CH2:25]Cl)=[O:17])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7]>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:6]([C:10]1[O:14][N:13]=[C:12]([NH:15][C:16]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:24](=[O:27])[CH2:25][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:17])[CH:11]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of pyrrolidine (33.43 mg; 0.47 mmol) and 4-dimethylaminopyridine (2 mg; 0.016 mmol) in DMF (1 mL) is added to (S)-1-(2-Chloro-acetyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide (77 mg; 0.235 mmol). The reaction mixture is heated at 60° C. for 18 hours. Purification by preparative HPLC provides the title compound, m/z 363 [M+H+].

Workup

customPurification by preparative HPLC

Sources & evidence

ORD record: ord-5d1c036eed004d85a4b348c02ad2489b
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889670B2

Reaction notes

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