Diisopropylethylamine → (S)-2-Chloro-4-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)pyrimidine-5-carbonitrile

HRID 75284Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:17]2[C:12](=[N:13][C:14]([C@@H:24]([NH2:26])[CH3:25])=[C:15]([C:18]3[N:22]([CH3:23])[N:21]=[CH:20][CH:19]=3)[CH:16]=2)[CH:11]=[CH:10]1.[Cl:27][C:28]1[N:33]=[C:32](Cl)[C:31]([C:35]#[N:36])=[CH:30][N:29]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[Cl:27][C:28]1[N:33]=[C:32]([NH:26][C@H:24]([C:14]2[N:13]=[C:12]3[CH:11]=[CH:10][N:9]([CH3:8])[C:17]3=[CH:16][C:15]=2[C:18]2[N:22]([CH3:23])[N:21]=[CH:20][CH:19]=2)[CH3:25])[C:31]([C:35]#[N:36])=[CH:30][N:29]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(S)-1-(1-Methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine 2,2,2-trifluoroacetate (100 mg, 0.271 mmol), 2,4-dichloropyrimidine-5-carbonitrile (70.7 mg, 0.406 mmol) and N-ethyl-N-isopropylpropan-2-amine (146 μL, 0.812 mmol) were combined in acetonitrile (1725 μL), and the resulting mixture was heated to 120° C. in a microwave reactor for 1 hour. The mixture was concentrated and purified on a silica gel column, eluting with EtOAc. The fractions were collected and concentrated in vacuo to give the title compound as a yellow solid (30 mg, 28%). ESI-MS m/z [M+H]+ calc'd for C19H17ClN8, 393.13; found 393.3.

Workup

concentrationThe mixture was concentrated
custompurified on a silica gel column
washeluting with EtOAc
customThe fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d6829d84fb7f411d81df52c5cfa82920
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835420B2

Reaction notes

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