6-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl ester → HCID 178518846, compound

HRID 855662Notes

Reaction equation

HRID 855662 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[C:10](=[O:18])[NH:9]1)=O)(C)(C)C.[CH:19]1([C:22]2[CH:23]=[C:24]([NH:27][C:28]3[N:33]=[C:32](Cl)[N:31]=[C:30]([Cl:35])[N:29]=3)[NH:25][N:26]=2)[CH2:21][CH2:20]1>C(O)CCC>[Cl:35][C:30]1[N:29]=[C:28]([NH:27][C:24]2[NH:25][N:26]=[C:22]([CH:19]3[CH2:21][CH2:20]3)[CH:23]=2)[N:33]=[C:32]([NH:17][C:14]2[CH:15]=[C:16]3[C:11]([C:10](=[O:18])[NH:9][NH:8]3)=[CH:12][CH:13]=2)[N:31]=1

Participants

4

Reactant 2

HCID 574980196-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl esterHCID 178478357HCID 178478357, compound

Product 1

HCID 178518846HCID 178518846, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

6-Amino-3-oxo-2,3-dihydro-indazole-1-carboxylic acid tert-butyl ester (69 mg, 0.277 mmol) and (5-Cyclopropyl-2H-pyrazol-3-yl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine (50 mg, 0.184 mmol) were taken into 1 ml of n-butanol and stirred at room temperature for 2 hours. The solvent was evaporated in vacuo and the resulting white solid residue dissolved in dichloromethane-trifluoro acetic acid (1:1 mixture, 2 ml. After 3 hours, the solvent was evaporated in vacuo and the crude product purified by prep HPLC to afford 15 mg of the desired product as a white solid (16.4% yield). H-NMR(DMSO-d6, 500 mHz) δ 11.11(m, 1H), 10.41(s, 1H), 10.29(s, 1H), 7.11–7.82(m, 3H), 6.04(s, 1H), 1.84(m, 1H), 0.89(m, 2H), 0.60(m, 2H). MS (ES+): m/e=384.0 (M+H), 382.0 (M−H); LC/Method A/3.891 min, 98.0% purity by area %.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe resulting white solid residue dissolved in dichloromethane-trifluoro acetic acid (1:1 mixture, 2 ml
  3. waitAfter 3 hours
  4. customthe solvent was evaporated in vacuo
  5. customthe crude product purified by prep HPLC

Sources & evidence

ORD record
ord-18e33feb2e734f02907eac25bd687aea
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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