Triethylamine → HCID 59496682, compound

HRID 449451Notes

Reaction equation

HRID 449451 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.[C:33]([C:35]1([CH2:39][C:40](O)=[O:41])[CH2:38][CH2:37][CH2:36]1)#[N:34].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>>[NH2:32][C:18]1[N:19]=[C:20]([C:22]2[CH:31]=[C:30]3[C:25]([CH2:26][CH2:27][N:28]([C:40](=[O:41])[CH2:39][C:35]4([C:33]#[N:34])[CH2:38][CH2:37][CH2:36]4)[CH2:29]3)=[CH:24][CH:23]=2)[CH:21]=[C:16]([N:13]2[CH2:12][CH2:11][N:10]([CH3:9])[CH2:15][CH2:14]2)[N:17]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 553036831246210-25-2HCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 59496682HCID 59496682, compound

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), (1-cyanocyclobutyl)acetic acid (5.3 mg, 0.038 mmol), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (17 mg, 0.038 mmol) in N,N-dimethylformate (0.5 mL). The mixture was stirred at r.t. for 30 min., and purified by RP-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=446.1.

Workup

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

Sources & evidence

ORD record
ord-4efb718e8af44878b71ee3828f7abe3b
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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