Ethanolamine → HCID 59136084, compound

HRID 1994953Notes

Reaction equation

HRID 1994953 reaction equation
[CH3:1][N:2]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][C:17]([C:20]1[S:21][CH:22]([CH2:25][CH:26]=O)[CH2:23][N:24]=1)=[CH:16]2)[S:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)(=[O:5])=[O:4].[NH2:28][CH2:29][CH2:30][OH:31].[BH4-].[Na+]>CO.C(OCC)(=O)C>[OH:31][CH2:30][CH2:29][NH:28][CH2:26][CH2:25][CH:22]1[S:21][C:20]([C:17]2[NH:18][C:19]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[N:2]([CH3:1])[S:3]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)(=[O:5])=[O:4])=[N:24][CH2:23]1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 4311764Sodium borohydrideHCID 57476377N-methyl-N-{2-[5-(2-oxoethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl)thiophene-2-sulfonamide

Product 1

HCID 59136084HCID 59136084, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methyl-N-{2-[5-(2-oxoethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide (300 mg) in methanol (5 mL) was added 2-aminoethanol (70 μL), and the mixture was stirred with heating under reflux for 4 hr. The reaction mixture was allowed to cool to room temperature, sodium borohydride (55 mg) was added, and the mixture was stirred for 30 min. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to give the title compound (220 mg, yield 67%) as a colorless amorphous solid from a fraction eluted with ethyl acetate-methanol (10:1, volume ratio). MS: 465 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. stirringthe mixture was stirred for 30 min
  4. washwashed with water and saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-368dbc35cbee4e11ac91166cd3048b59
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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