Hydrochloric Acid → HCID 178494224, compound

HRID 1176048Notes

Reaction equation

HRID 1176048 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)[N:5]=[C:4]([NH:17][C:18]2[CH:26]=[C:25]3[C:21]([C:22](=[O:27])[NH:23][NH:24]3)=[CH:20][CH:19]=2)[N:3]=1.Cl.[CH3:29][O-:30].[Na+]>CO>[CH:14]1([C:12]2[CH:13]=[C:9]([NH:8][C:6]3[N:7]=[C:2]([O:30][CH3:29])[N:3]=[C:4]([NH:17][C:18]4[CH:26]=[C:25]5[C:21]([C:22](=[O:27])[NH:23][NH:24]5)=[CH:20][CH:19]=4)[N:5]=3)[NH:10][N:11]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 178518846HCID 178518846, compound

Product 1

HCID 178494224HCID 178494224, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(6-[4-Chloro-6-(5-cyclopropyl-2H-pyrazol-3-ylamino)-[1,3,5]triazin-2-ylamino]-1,2-dihydro-indazol-3-one (70 mg, 0.14 mmol) was dissolved in 6 ml of 0.5 M solution of sodium methoxide in methanol and stirred at room temperature for 3 hours. The reaction was neutralized to pH 6-7 with 0.5 N hydrogen chloride. The cloudy solution was concentrated in vacuo. The resulting yellow solid was suspended in water, filtered, then purified by prep HPLC to afford 7.5 mg of the desired product as a white solid (10.8% yield). H-NMR (DMSO-d6, 500 mHz) δ 10.96 (s br, 1H), 9.76 (s br, 1H), 7.90 (s br, 1H), 7.44 (d, 1H), 7.18 (m, 1H), 6.02 (s br, 1H) 3.85 (s, 3H), 1.80 (s br, 1H), 0.84 (m, 2H), 0.61 (s br, 2H). MS (ES+): m/e=380.1 (M+H), 378.1 (M-H); LC/Method A/3.543 min, 90.0% purity by area %.

Workup

  1. concentrationThe cloudy solution was concentrated in vacuo
  2. filtrationfiltered
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-943f9d959fb646b18719502441460c5c
Source dataset
uspto-grants-2010_11
Patent number
US07842712B2

Reaction notes

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