Triethylamine → 4-Amino-N-(4-chlorobenzyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 1470286Notes

Reaction equation

Cl.Cl.[Cl:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][NH:9][C:10]([C:12]2([NH2:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1.Cl[C:22]1[C:23]2[CH:30]=[CH:29][NH:28][C:24]=2[N:25]=[CH:26][N:27]=1.C(N(CC)CC)C>C(O)CCC>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10]([C:12]2([NH2:18])[CH2:13][CH2:14][N:15]([C:22]3[C:23]4[CH:30]=[CH:29][NH:28][C:24]=4[N:25]=[CH:26][N:27]=3)[CH2:16][CH2:17]2)=[O:11])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A degassed mixture of 4-amino-piperidine-4-carboxylic acid 4-chloro-benzylamide dihydrochloride (48 mg, 0.13 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (21 mg, 0.12 mmol), triethylamine (126 uL, 0.9 mmol) and n-butanol (1.2 mL) was stirred at 100° C. for 18 h. The solvents were removed by evaporation and the crude mixture was first purified on a SCX-II acid resin, eluting with methanol then 2M ammonia/methanol, and then by preparative TLC, eluting with 10% methanol in dichloromethane, to give 4-amino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidine-4-carboxylic acid 4-chloro-benzylamide (37 mg, 0.096 mmol, 80%). LC-MS (LCT2) m/z 385 [M+H+], R, 2.84 min.

Workup

customThe solvents were removed by evaporation
customthe crude mixture was first purified on a SCX-II acid resin
washeluting with methanol
wash2M ammonia/methanol, and then by preparative TLC, eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-66a6f018d7e446bbabd1ed9a7948bf83
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006430B2

Reaction notes

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