1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-{3-[2-(2-Chloro-4-fluorophenyl)acetylamino]phenyl}-1H-indazole-5-carboxamide

HRID 1349853Notes

Reaction equation

HRID 1349853 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[CH2:34][C:35](O)=[O:36].CCN=C=NCCCN(C)C>>[Cl:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[CH2:34][C:35]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1)=[O:36]

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27250612-(2-Chloro-4-fluorophenyl)acetic acidHCID 224799593-(3-Aminophenyl)-1-perhydro-2h-pyran-2-yl-1h-indazole5-carboxamide

Product 1

HCID 224799283-{3-[2-(2-Chloro-4-fluorophenyl)acetylamino]phenyl}-1H-indazole-5-carboxamideYield 16%

Procedure

Following Example 290, the reaction of 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide (200 mg, 0.56 mmol) with 2-chloro-4-fluorophenylacetic acid (0.13 g, 0.71 mmol) and EDCI (0.17 g, 0.89 mmol) furnished 38 mg (14% yield) of the title compound. 1H NMR (DMSO-d6) δ 10.4 (s, 1H), 8.6 (s, 1H), 8.1 (br s, 1H), 7.9 (dd, 1H), 7.75 (m, 2H), 7.65 (d, 1H), 7.52–7.4 (m, 3H), 7.35 (s, 1H), 7.2 (m, 1H), 3.9 (s, 2H); ES-MS (m/z) 423 [M]+.

Sources & evidence

ORD record
ord-64b64a92ba27458fa33c00c0139452cf
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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