Acrylonitrile → 3-(3-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-1H-pyrazol-1-yl}propanenitrile

HRID 2090390Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([N:14]3[CH:23]([CH3:24])[CH2:22][C:21]4[C:16](=[CH:17][C:18]([C:25]5[CH:29]=[CH:28][NH:27][N:26]=5)=[CH:19][CH:20]=4)[CH2:15]3)[N:11]=[C:10]([NH2:30])[N:9]=2)[CH2:4][CH2:3]1.[C:31](#[N:34])[CH:32]=[CH2:33].N12CCCN=C1CCCCC2>C(#N)C>[NH2:30][C:10]1[N:11]=[C:12]([N:14]2[CH:23]([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][C:18]([C:25]4[CH:29]=[CH:28][N:27]([CH2:33][CH2:32][C:31]#[N:34])[N:26]=4)=[CH:19][CH:20]=3)[CH2:15]2)[CH:13]=[C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-(4-methylpiperazin-1-yl)-6-[3-methyl-7-(1H-pyrazol-3-yl)-3,4-dihydroisoquinolin-2(1H)-yl]pyrimidin-2-amine (10.0 mg, 0.0247 mmol), 2-propenenitrile (50.0 uL, 0.761 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (5.0 uL, 0.033 mmol) in acetonitrile (0.15 mL) was heated at 50° C. for 2 h. The mixture was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=458.3.

Workup

customThe mixture was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record: ord-84df59dbe11549e5a7e1783694be4628
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436008B2

Reaction notes

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