6-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl ester → HCID 178518844, compound

HRID 855669Notes

Reaction equation

HRID 855669 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:10][N:11]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[CH:13]=2)[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=1.C(OC([N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([NH2:36])[CH:34]=2)[C:29](=[O:37])[NH:28]1)=O)(C)(C)C>>[CH:14]1([C:12]2[CH:13]=[C:9]([NH:8][C:6]3[N:7]=[C:2]([NH:36][C:33]4[CH:34]=[C:35]5[C:30]([C:29](=[O:37])[NH:28][NH:27]5)=[CH:31][CH:32]=4)[CH:3]=[CH:4][C:5]=3[N+:17]([O-:19])=[O:18])[NH:10][N:11]=2)[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 574980196-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl esterHCID 178526632HCID 178526632, compound

Product 1

HCID 178518844HCID 178518844, compoundYield 16.2%

Procedure

6-[6-(5-Cyclopropyl-2H-pyrazol-3-ylamino)-5-nitro-pyridin-2-ylamino]-1,2-dihydro-indazol-3-one was prepared by the reaction of (6-Chloro-3-nitro-pyridin-2-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine and 6-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl ester in a similar manner as described above to afford 17 mg of the desired product as a bright yellow solid (16.2% yield). H-NMR (CD3OD) δ 8.32(d, 1H), 7.68(d, 1H), 7.65(s, 1H), 7.17(d, 1H), 6.38(d, 1H), 6.24(s, 1H), 1.79(m, 1H), 0.84(m, 2H), 0.48(m, 2H). MS (ES+): m/e=393.2 (M+H), 391.2 (M−H); LC/Method A/4.149 min, 100% purity by area %.

Sources & evidence

ORD record
ord-807cfa47c6224515ae0afbdfeb6414c1
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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