Ethanolamine → N-[2-(5-{2-[(2-hydroxyethyl)amino]ethyl}-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide

HRID 1994953노트

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HRID 1994953 반응식
[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

참가 물질

6

반응물 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

생성물 1

HCID 59136084N-[2-(5-{2-[(2-hydroxyethyl)amino]ethyl}-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide수율 67%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-368dbc35cbee4e11ac91166cd3048b59
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652133B2

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