Piperidine → N-{4-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzyl}-2-piperidin-1-yl-acetamide

HRID 1295643Notes

Reaction equation

Cl[CH2:2][C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:30][C:16]3[N:17]=[CH:18][N:19]=[C:20]([NH:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:23])[C:15]=3[CH:14]=2)=[CH:9][CH:8]=1)=[O:4].[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(O)CCC>[C:24]1([C@H:22]([NH:21][C:20]2[C:15]3[CH:14]=[C:13]([C:10]4[CH:11]=[CH:12][C:7]([CH2:6][NH:5][C:3](=[O:4])[CH2:2][N:31]5[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]5)=[CH:8][CH:9]=4)[NH:30][C:16]=3[N:17]=[CH:18][N:19]=2)[CH3:23])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 80 mg (0.19 mmol) 2-chloro-N-{4-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzyl}-acetamide in 1.5 ml n-butanol is treated with 47 μl (0.48 mmol) piperidine and then heated to 100° C. for 2 h. The clear solution is cooled and the solvent evaporated. The residue is purified with flash chromatography using a mixture of ethyl acetate/methanol with increasing concentrations of methanol starting with 100:2.5 and ending with 10:1. The title compound is obtained as a colorless powder; m.p. 194-196° C.; MS-ES+: (M+H)+=469.

Workup

temperatureThe clear solution is cooled
customthe solvent evaporated
customThe residue is purified with flash chromatography
additiona mixture of ethyl acetate/methanol
temperaturewith increasing concentrations of methanol starting with 100:2.5

Sources & evidence

ORD record: ord-cb1bc46cc05e4c33a2872211ebc71f0e
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244729B2

Reaction notes

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