Dimethylamine → HCID 178483055, compound

HRID 1176049Notes

Reaction equation

HRID 1176049 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.[CH3:28][NH:29][CH3:30]>C1COCC1>[CH:14]1([C:12]2[CH:13]=[C:9]([NH:8][C:6]3[N:7]=[C:2]([N:29]([CH3:30])[CH3:28])[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

4

Reactant 2

HCID 674DimethylamineHCID 178518846HCID 178518846, compound

Product 1

HCID 178483055HCID 178483055, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-[4-Chloro-6-(5-cyclopropyl-2H-pyrazol-3-ylamino)-[1,3,5]triazin-2-ylamino]-1,2-dihydro-indazol-3-one (60 mg, 0.121 mmol) was dissolved in 5 ml of a 2 M solution of dimethylamine in THF and stirred at room temperature for 2 hours. The reaction was concentrated in vacuo and purified on prep HPLC to afford 38 mg (62% yield) of the desired product as a white solid (62.2% yield). H-NMR (DMSO-d6, 500 mHz) δ 11.20 (s, 1H), 10.48 (s br, 1H), 10.08 (s, 1H), 7.92 (s, 1H), 7.55 (d, 1H), 7.13 (s, 1H), 5.93 (s, 1H), 3.20 (d, 6H), 1.92 (m, 1H), 0.96 (m, 2H), 0.72 (m, 2H). MS (ES+): m/e=393.2 (M+H), 391.2 (M-H); LC/Method A/3.835 min, 98.0% purity by area %.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified on prep HPLC

Sources & evidence

ORD record
ord-bd3d8f4d6b8a43289f2f8a1a0c66b42f
Source dataset
uspto-grants-2010_11
Patent number
US07842712B2

Reaction notes

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