1,1'-Carbonyldiimidazole → 1H-Indazole-3-carboxamide, N-[2-(4-morpholinyl)ethyl]-

HRID 2256359Notes

Reaction equation

HRID 2256359 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[N:28]1([CH2:27][CH2:26][NH:25][C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:12])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 78250Indazole-3-carboxylic acidHCID 4082852-Morpholinoethylamine

Product 1

HCID 105164521H-Indazole-3-carboxamide, N-[2-(4-morpholinyl)ethyl]-Yield 24.3%

Procedure

Same procedure followed as described in Example 1. The following amounts were used: 1H-indazole-3-carboxylic acid (0.65 g, 4 mmol), 1,1'-carbonyldiimidazole (0.65 g, 4 mmol) and 4-(2-aminoethyl)morpholine (0.52 mL, 4 mmol). The ethyl acetate extracts were evaporated to 0.468 g solid. Crystallization from ethyl acetate provided 0.267 g colorless crystals. Mass spectrum, m+ =274.

Workup

  1. customThe ethyl acetate extracts were evaporated to 0.468 g solid
  2. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-a1132e9fa8b046698ffcb0913bd7d114
Source dataset
uspto-grants-1997_08
Patent number
US05654320

Reaction notes

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