Imidazole → 4-[Cyclopropyl-(2-imidazol-1-yl-pyrimidine-5-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1409696Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:18]([C:20]2[CH:21]=[N:22][C:23](Cl)=[N:24][CH:25]=2)=[O:19])[CH:15]2[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[NH:36]1[CH:40]=[CH:39][N:38]=[CH:37]1.O>CN1CCCC1=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:15]2[CH2:17][CH2:16]2)[C:18]([C:20]2[CH:21]=[N:22][C:23]([N:36]3[CH:40]=[CH:39][N:38]=[CH:37]3)=[N:24][CH:25]=2)=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-[(2-chloro-pyrimidine-5-carbonyl)-cyclopropyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (3.00 g), ethyldiisopropylamine (1.97 mL) and 1H-imidazole (520 mg) in N-methyl-2-pyrrolidinon (10 mL) is stirred over night at 100° C. After cooling to room temperature, water is added and the precipitate is filtered off and dried. LC (method 9): tR=1.29 min; Mass spectrum (ESI+): m/z=413 [M+H]+.

Workup

temperatureAfter cooling to room temperature
filtrationthe precipitate is filtered off
customdried

Sources & evidence

ORD record: ord-4233bdaa9f154df792273ad5ab302717
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921398B2

Reaction notes

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