Hydrochloric Acid → HCID 178494224, compound

HRID 855663Notes

Reaction equation

HRID 855663 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-dafb3088372440da89e5c19a5e20806d
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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