Water → HCID 68907744, compound

HRID 546512Notes

Reaction equation

HRID 546512 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]1[NH2:21])=[O:13])=[CH:6]2.C(N(CC)CC)C.[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[S:34](Cl)(=[O:36])=[O:35].O>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]1[NH:21][S:34]([C:30]1[S:29][CH:33]=[CH:32][CH:31]=1)(=[O:36])=[O:35])=[O:13])=[CH:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 18442849HCID 18442849, compound

Product 1

HCID 68907744HCID 68907744, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-cis-N-[(5-Chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride (200 mg) was dissolved in N,N-dimethylformamide (1 ml), and triethylamine (0.28 ml) and 2-thiophenesulfonyl chloride (111 mg) were added to stir the mixture for 75 minutes. Water was added to the reaction mixture, and deposit was collected by filtration and recrystallized from methanol to obtain the title compound (198 mg) as colorless crystals.

Workup

  1. filtrationwas collected by filtration
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-f886d4e61323422da78eb83f8d9f3e0e
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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