Diisopropylethylamine → (1S,3S)-N-[2,2-difluoro-2-(4-methylphenyl)ethyl]-N'-[2-(tetrahydro-2H-pyran-2-yl)-2H-pyrazolo[3,4-d]pyrimidin-4-yl]cyclopentane-1,3-diamine

HRID 271394Notes

Reaction equation

[F:1][C:2]([F:18])([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[CH2:3][NH:4][C@H:5]1[CH2:9][CH2:8][C@H:7]([NH2:10])[CH2:6]1.Cl[C:20]1[C:21]2[C:22](=[N:26][N:27]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[CH:28]=2)[N:23]=[CH:24][N:25]=1.C(N(C(C)C)CC)(C)C>C(O)CCC>[F:1][C:2]([F:18])([C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1)[CH2:3][NH:4][C@H:5]1[CH2:9][CH2:8][C@H:7]([NH:10][C:20]2[C:21]3[C:22](=[N:26][N:27]([CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][O:30]4)[CH:28]=3)[N:23]=[CH:24][N:25]=2)[CH2:6]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (1S,3S)-N-[2,2-difluoro-2-(4-methylphenyl)ethyl]cyclopentane-1,3-diamine (627 mg, 2.46 mmol), 4-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-pyrazolo[3,4-d]pyrimidine (588 mg, 2.46 mmol), n-butanol (1.6 mL) and diisopropylethylamine (1.6 mL) was heated in microwave for 15 min at 150° C. The reaction mixture was concentrated in vacuo to a viscous brown oil, which was purified by silica gel chromatography (CH2Cl2/MeOH gradient) to give the title compound (0.982 g) as a cream colored foam: MS=457.4 (M+1).

Workup

concentrationThe reaction mixture was concentrated in vacuo to a viscous brown oil, which
customwas purified by silica gel chromatography (CH2Cl2/MeOH gradient)

Sources & evidence

ORD record: ord-e613211b8b2a4627acd82955199aa802
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452893B2

Reaction notes

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