Methylhydrazine → HCID 57889020, compound

HRID 1820183Notes

Reaction equation

HRID 1820183 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:31])[C@H:15]([NH:19][C:20]3[NH:24][N:23]=[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:21]=3)[CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:32]NN>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:31])[C@H:15]([NH:19][C:20]3[N:24]([CH3:32])[N:23]=[C:22]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:21]=3)[CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 178448312HCID 178448312, compound

Product 1

HCID 57889020HCID 57889020, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-1-(4-(4-Chlorophenyl)piperidin-1-yl)-3-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylamino)butan-1-one (40 mg, 0.09 mmol) was dissolved in THF (0.5 mL) and then treated with MeNHNH2 (10 μL, excess). The reaction was stirred at rt. overnight. After this time, the THF was removed in vacuo and the remains were taken up in MeOH and then purified by preparative HPLC to give (R)-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-ylamino)butan-1-one (18 mg, 47%) as a 90/10 mixture of N1—CH3/N2—CH3 isomers. MS found: 452 (M+H).

Workup

  1. customovernight
  2. customAfter this time, the THF was removed in vacuo
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b5f0ffc80d194588b03e345c28d36c57
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

Loading…