Triethylamine → 1-[4-[3-Hydroxy-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamide

HRID 928620Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

8-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-ol (44 mg, 0.12 mmol) was suspended in acetonitrile (3 mL). Pyrrolidine-3-carboxamide hydrochloride (36 mg, 0.24 mmol) and triethylamine (0.067 mL, 0.47 mmol) were added and the mixture was heated to 150° C. for 30 min in a microwave (twice). Further batches of pyrrolidine-3-carboxamide hydrochloride (36 mg, 0.24 mmol) and triethylamine (0.067 mL, 0.47 mmol) were added and the mixtures were heated to 150° C. for 30 min in a microwave. The solvent was evaporated and the residue was purified by LCUV (acidic method 1) to give the target compound as a white solid (44 mg). m/z [M+H]+450.1. Retention time 3.75 min (LCMS method+ve 6 min).

Workup

temperaturethe mixtures were heated to 150° C. for 30 min in a microwave
customThe solvent was evaporated
customthe residue was purified by LCUV (acidic method 1)

Sources & evidence

ORD record: ord-689dfd6514304ac09fe436377edaa063
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290511B2

Reaction notes

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