Pyrrolidine-3-carboxamide → 1-[4-[4-[[Methyl-(1-methylpyrrolidin-3-yl)amino]methyl]-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamide

HRID 928561Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][N:24]([CH3:31])[CH:25]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26]3)[CH2:19][CH2:18]2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[NH:32]1[CH2:36][CH2:35][CH:34]([C:37]([NH2:39])=[O:38])[CH2:33]1>C(#N)C>[CH3:31][N:24]([CH2:23][CH:20]1[CH2:21][CH2:22][N:17]([C:4]2[C:5]3[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:9][S:8][C:6]=3[N:7]=[C:2]([N:32]3[CH2:36][CH2:35][CH:34]([C:37]([NH2:39])=[O:38])[CH2:33]3)[N:3]=2)[CH2:18][CH2:19]1)[CH:25]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26]1

Participants

Conditions

Temperature: 140 °C

Procedure

N—[[1-(2-chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methyl]-N,1-dimethyl-pyrrolidin-3-amine (100 mg, 0.219 mmol) and pyrrolidine-3-carboxamide (300 mg, 2.63 mmol) were stirred in dry acetonitrile (1.5 ml) and heated in a microwave at 140° C. for 0.5 h. The solvent was evaporated and the crude residue purified by flash column chromatography (0 to 5% 7.0M NH3/MeOH in dichloromethane) to give 1-[4-[4-[[methyl-(1-methylpyrrolidin-3-yl)amino]methyl]-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamide as an off white solid (25 mg, 21%). m/z (M+H)+534.3, RT=2.69 min.

Workup

customThe solvent was evaporated
customthe crude residue purified by flash column chromatography (0 to 5% 7.0M NH3/MeOH in dichloromethane)

Sources & evidence

ORD record: ord-cf29f102aea4415d9e3df9d78a71e38b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290511B2

Reaction notes

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