Cyclopropanecarboxylic acid → HCID 70119988, compound

HRID 2183346Notes

Reaction equation

HRID 2183346 reaction equation
N[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.[CH:26]1([C:29]([OH:31])=O)[CH2:28][CH2:27]1.CC[N:34]=C=NCCCN(C)C>>[CH:26]1([C:29]([NH:34][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=2[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)=[O:31])[CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 15655Cyclopropanecarboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 224799593-(3-Aminophenyl)-1-perhydro-2h-pyran-2-yl-1h-indazole5-carboxamide

Product 1

HCID 70119988HCID 70119988, compoundYield 26%

Procedure

Following Example 290, the reaction of 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide (600 mg, 1.79 mmol) with cyclopropanecarboxylic acid (0.43 mL, 0.46 g, 5.4 mmol) and EDCI (1.06 g, 5.4 mmol) furnished 140 mg (26% yield) of the title compound. 1H NMR (DMSOd6) δ 13.4 (br s, 1H), 10.4 (s, 1H), 8.6 (s, 1H), 8.2 (s, 1H), 8.1 (br s, 1H), 7.9 (dd, 1H), 7.75 (m, 2H), 7.6 (d, 1H), 7.5 (t, 1H), 7.35 (s, 1H), 1.9-1.68 (m, 1H), 0.8 (m, 4H); ES-MS (m/z) 321 [M+H]+.

Sources & evidence

ORD record
ord-c4fe74ef038a4ca59b8acca4bc26a928
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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