Diisopropylethylamine → HCID 117899602, compound

HRID 522293Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][NH2:10])[CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.F[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]3[CH:37]=[CH:36][NH:35][C:29]=3[N:30]=[C:31]([C:33]#[N:34])[N:32]=2)=[CH:23][C:22]=1[C:38]([F:41])([F:40])[F:39]>CN1CCCC1=O>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][NH:10][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[C:28]4[CH:37]=[CH:36][NH:35][C:29]=4[N:30]=[C:31]([C:33]#[N:34])[N:32]=3)=[CH:23][C:22]=2[C:38]([F:39])([F:40])[F:41])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 140 °C

Procedure

2-(1-Methylpiperidin-4-yl)ethanamine (93 mg) and N,N-diisopropylethylamine (0.22 mL) were added to a mixture of 4-[4-fluoro-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (100 mg) and N-methylpyrrolidone (2 mL), and the mixture was stirred at 140° C. for 1 hour under microwave irradiation. After the reaction mixture was cooled to room temperature, the reaction mixture was purified by silica gel column chromatography (CHCl3:MeOH=98:2 to 85:15), whereby 4-[4-{[2-(1-methylpiperidin-4-yl)ethyl]amino}-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (66 mg) was obtained as a white solid.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customthe reaction mixture was purified by silica gel column chromatography (CHCl3:MeOH=98:2 to 85:15)

Sources & evidence

ORD record: ord-062263a1b54c489996da1bede907c3ae
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328118B2

Reaction notes

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