2-Phenylpropionic acid → HCID 22480004, compound

HRID 2183356Notes

Reaction equation

HRID 2183356 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.[C:26]1([CH:32]([CH3:36])[C:33](O)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CCN=C=NCCCN(C)C>>[C:26]1([CH:32]([CH3:36])[C:33]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[CH:15]=4)[NH:10][N:9]=3)[CH:5]=[CH:6][CH:7]=2)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 102962-Phenylpropionic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 224799593-(3-Aminophenyl)-1-perhydro-2h-pyran-2-yl-1h-indazole5-carboxamide

Product 1

HCID 22480004HCID 22480004, compoundYield 18.6%

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-phenylpropionic acid (97 μL, 0.11 g, 0.71 mmol) and EDCI (0.17 g, 0.89 mmol) furnished 40 mg (17% yield) of the title compound. 1H NMR (DMSO-d6) δ 13.5 (s, 1H), 10.3 (s, 1H), 8.6 (s, 1H), 8.2 (br s, 1H), 8.35 (br s, 1H), 7.94 (dd, 1H), 7.7 (m, 2H), 7.6 (d, 1H), 7.5-7.3 (m, 5H), 7.25 (m, 1H), 3.8 (s, 1H), 1.4 (d, 3H); ES-MS (m/z) 385 [M+H]+.

Sources & evidence

ORD record
ord-f635ec5c738d496a96a86f13193d14a5
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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