5-amino-1-phenyl-1H-pyrazole-3,4-dicarboxylic acid diethyl ester → 6-Biphenyl-4-yl-5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid ethyl ester

HRID 1693518Notes

Reaction equation

HRID 1693518 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13]CC)=O)=[C:9]([NH2:16])[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:7]=1)=[O:5])[CH3:2].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31](Cl)[C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:34][CH:33]=2)=[CH:26][CH:25]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[C:11](=[O:13])[N:30]([C:27]3[CH:26]=[CH:25][C:24]([Cl:23])=[CH:29][CH:28]=3)[C:31]([C:32]3[CH:37]=[CH:36][C:35]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[CH:34][CH:33]=3)=[N:16][C:9]=2[N:8]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 578979175-amino-1-phenyl-1H-pyrazole-3,4-dicarboxylic acid diethyl esterHCID 86241256N-(4-chloro-phenyl)-biphenyl-4-carboximidoyl chloride

Product 1

HCID 116853556-Biphenyl-4-yl-5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid ethyl ester

Procedure

6-Biphenyl-4-yl-5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid ethyl ester is prepared from 5-amino-1-phenyl-1H-pyrazole-3,4-dicarboxylic acid diethyl ester and N-(4-chloro-phenyl)-biphenyl-4-carboximidoyl chloride by following a similar procedure as described in example 2 and purified by preparative LC/MS. 1H NMR (CDCfe) δ(ppm) 8.14(d, 2H), 7.36˜7.57(m, 12H), 7.33(d, 2H), 7.14(d, 2H), 4.53(q, 2H), 1.46(t, 3H); HPLC-MS calculated for C32H23ClN4O3 (M+H+): 547.2. Found: 547.2.

Workup

  1. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-b0fd86d082a74d87a4227d6626f6f605
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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