Cyclopentanecarbonyl chloride → 1-(Cyclopentylcarbonyl)piperidin-4-yl 7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3,4-dihydroisoquinoline-2(1h)-carboxylate

HRID 449380Notes

Reaction equation

HRID 449380 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:10][C:11]1[N:16]=[C:15]([C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][N:23]([C:27]([O:29][CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)=[O:28])[CH2:24]3)=[CH:19][CH:18]=2)[CH:14]=[C:13]([N:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[N:12]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[NH2:10][C:11]1[N:16]=[C:15]([C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][N:23]([C:27]([O:29][CH:30]4[CH2:35][CH2:34][N:33]([C:6]([CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)=[O:7])[CH2:32][CH2:31]4)=[O:28])[CH2:24]3)=[CH:19][CH:18]=2)[CH:14]=[C:13]([N:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[N:12]=1

Participants

5

Reactant 3

HCID 78284Cyclopentanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 67541330piperidin-4-yl 7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate HCl salt

Product 1

HCID 594966511-(Cyclopentylcarbonyl)piperidin-4-yl 7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3,4-dihydroisoquinoline-2(1h)-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cyclopentanecarbonyl chloride (2.0 uL, 0.016 mmol) was added to a mixture of piperidin-4-yl 7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate HCl salt (6.0 mg, 0.011 mmol) and N,N-diisopropylethylamine (9.3 uL, 0.054 mmol) in acetonitrile (0.4 mL). The reaction mixture was stirred at r.t. for 30 min., purified by RP-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=548.3.

Workup

  1. custompurified by RP-LCMS (pH=10)

Sources & evidence

ORD record
ord-2e928e5c660b429394838b972ec9551b
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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