Hydrazine hydrate (1:1) → HCID 86672764, compound

HRID 1754959Notes

Reaction equation

HRID 1754959 reaction equation
O.NN.C([NH:12][C:13](=[S:47])[N:14]([C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([CH2:23][CH2:24][S:25]([N:28]2[CH2:45][CH2:44][C:31]3([N:35]=[C:34]([CH:36]4[CH2:41][CH2:40][CH:39]([CH3:42])[CH2:38][CH2:37]4)[NH:33][C:32]3=[O:43])[CH2:30][CH2:29]2)(=[O:27])=[O:26])=[C:18]([CH3:46])[CH:17]=1)[CH3:15])(=O)C1C=CC=CC=1>C(O)C>[CH3:46][C:18]1[CH:17]=[C:16]([N:14]([CH3:15])[C:13]([NH2:12])=[S:47])[CH:21]=[C:20]([CH3:22])[C:19]=1[CH2:23][CH2:24][S:25]([N:28]1[CH2:45][CH2:44][C:31]2([N:35]=[C:34]([CH:36]3[CH2:37][CH2:38][CH:39]([CH3:42])[CH2:40][CH2:41]3)[NH:33][C:32]2=[O:43])[CH2:30][CH2:29]1)(=[O:26])=[O:27]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86672763HCID 86672763, compound

Product 1

HCID 86672764HCID 86672764, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (55 mg, 1.1 mmol) was added to a solution of 3-benzoyl-1-(3,5-dimethyl-4-{2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-phenyl)-1-methyl-thiourea (140 mg, 0.22 mmol) in ethanol (7 ml). The mixture was stirred at room temperature for 15 hours and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give 1-(3,5-dimethyl-4-{2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-phenyl)-1-methyl-thiourea (119 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-9a6885fa26b344d581d0a76a590783ce
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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