Triethylamine → 1-[7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3,4-dihydro-1H-isoquinolin-2-yl]-2-cyclopentylethanone

HRID 449343Notes

Reaction equation

HRID 449343 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[C:20]([C:22]3[CH:31]=[C:30]4[C:25]([CH2:26][CH2:27][NH:28][CH2:29]4)=[CH:24][CH:23]=3)[N:19]=[C:18]([NH2:32])[N:17]=2)[CH2:12][CH2:11]1.[CH:33]1([CH2:38][C:39](O)=[O:40])[CH2:37][CH2:36][CH2:35][CH2:34]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>>[CH:33]1([CH2:38][C:39]([N:28]2[CH2:27][CH2:26][C:25]3[C:30](=[CH:31][C:22]([C:20]4[CH:21]=[C:16]([N:13]5[CH2:12][CH2:11][N:10]([CH3:9])[CH2:15][CH2:14]5)[N:17]=[C:18]([NH2:32])[N:19]=4)=[CH:23][CH:24]=3)[CH2:29]2)=[O:40])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 71606Cyclopentylacetic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 594967621-[7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3,4-dihydro-1H-isoquinolin-2-yl]-2-cyclopentylethanone

Procedure

Triethylamine (24 uL, 0.17 mmol) was added to a mixture of 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt (15 mg, 0.034 mmol), cyclopentaneacetic acid (5.2 uL, 0.041 mmol) (Aldrich, Cat. #125490), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (17 mg, 0.038 mmol) (Chem-Impex, Cat. #00604) in N,N-dimethylformate (0.5 mL). The mixture was stirred at r.t. for 30 min., and then purified by RP-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=435.2.

Workup

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

Sources & evidence

ORD record
ord-bee29ed5da99409fa15959ec835e3bbd
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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