2-Mercaptoethanol → HCID 57901698, compound

HRID 1851630Notes

Reaction equation

HRID 1851630 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[N:17]([CH2:26][CH2:27][O:28][CH2:29][CH3:30])[S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])=[N:5][CH:4]=1.C(N(CC)CC)C.[SH:38][CH2:39][CH2:40][OH:41]>CN(C)C=O.O>[CH2:29]([O:28][CH2:27][CH2:26][N:17]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[NH:9][C:8]([C:6]1[S:7][C:3]([CH2:2][S:38][CH2:39][CH2:40][OH:41])=[CH:4][N:5]=1)=[CH:16]2)[S:18]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)(=[O:19])=[O:20])[CH3:30]

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 59136056HCID 59136056, compound

Product 1

HCID 57901698HCID 57901698, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution (2 mL) of N-{2-[5-(chloromethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-(2-ethoxyethyl)thiophene-2-sulfonamide (18 mg) and triethylamine (14 mg), 2-mercaptoethanol (10 mg) in N,N-dimethylformamide was stirred at room temperature for 18 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate. The extract was concentrated, and the residue was purified by preparative HPLC to give the title compound (5.9 mg, yield 30%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe extract was concentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-85f649776f4040dc95aed4347af02366
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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