Hydrazine → HCID 178448312, compound

HRID 1820182Notes

Reaction equation

HRID 1820182 reaction equation
[C:1](/[N:9]=[C:10](\SC)/[NH:11][C@H:12]([CH:28]([CH3:30])[CH3:29])[C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=[O:14])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:33][NH2:34]>C1COCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH:18]2[CH2:19][CH2:20][N:15]([C:13](=[O:14])[C@H:12]([NH:11][C:10]3[NH:34][N:33]=[C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[N:9]=3)[CH:28]([CH3:30])[CH3:29])[CH2:16][CH2:17]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 178503944HCID 178503944, compound

Product 1

HCID 178448312HCID 178448312, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R,Z)-Methyl N′-benzoyl-N-(1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamimidothioate (47 mg, 0.1 mmol) was dissolved in THF (0.5 mL) and treated with anhydrous hydrazine (10 μL, 0.3 mmol). The reaction was stirred at rt. overnight. After this time, the THF was removed in vacuo and the resulting residue was dissolved in methanol and then purified by preparative HPLC to give (R)-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylamino)butan-1-one (20 mg, 45%). MS found: 438 (M+H).

Workup

  1. customovernight
  2. customAfter this time, the THF was removed in vacuo
  3. dissolutionthe resulting residue was dissolved in methanol
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-2ec8d2389029420ba18a94d0760890a3
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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