Indazole-3-carboxylic acid → HCID 10428804, compound

HRID 374104Notes

Reaction equation

[NH2:1][CH:2]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5][N:4]([CH3:16])[CH2:3]1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26](O)=[O:27])=[N:18]1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:9]([N:7]1[CH2:8][CH:2]([NH:1][C:26]([C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:17][N:18]=2)=[O:27])[CH2:3][N:4]([CH3:16])[CH2:5][CH2:6]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 6-amino-1-benzyl-4-methylhexahydro-1H-1,4-diazepine (1.0 g) in dichloromethane (20 ml), 1H-indazole-3-carboxylic acid (740 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (877 mg) are added, and the resulting mixture is stirred at 25° C. for 2 hours. The reaction mixture is washed successively with water and 10% aqueous sodium hydroxide solution, and dried over magnesium sulfate. The solvent is evaporated under reduced pressure, and the residue is chromatographed on silica gel with elution of acetone. Fractions containing the title compound are pooled and evaporated under reduced pressure to give the title compound (0.9 g) as an oil. The free base thus obtained is converted to the hemifumarate of the title compound in a usual manner, m.p. 192°-194° C. (recrystallized from ethanol).

Workup

washThe reaction mixture is washed successively with water and 10% aqueous sodium hydroxide solution
dry with materialdried over magnesium sulfate
customThe solvent is evaporated under reduced pressure
customthe residue is chromatographed on silica gel with elution of acetone
additionFractions containing the title compound
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-fea217bdc23f46d0a98aaa52d0692b3f
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166341

Reaction notes

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