1-Hydroxybenzotriazole → N-[3-(2-hydroxyethyl)phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide

HRID 15860

반응식

HRID 15860 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[CH3:11][C:12]1[S:13][C:14]([C:18](O)=[O:19])=[C:15]([CH3:17])[N:16]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[OH:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([NH:1][C:18]([C:14]2[S:13][C:12]([CH3:11])=[N:16][C:15]=2[CH3:17])=[O:19])[CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 149389872-(3-Aminophenyl)ethan-1-ol

생성물 1

HCID 57444343N-[3-(2-hydroxyethyl)phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide수율 73%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-(3-Aminophenyl)ethanol (1.202 g, 8.76 mmol) was added to a solution of 2,4-dimethyl-1,3-thiazole-5-carboxylic acid (1.652 g, 10.51 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.015 g, 10.51 mmol) and 1-hydroxybenzotriazole (1.420 g, 10.51 mmol) in dry DMF (20 mL). The mixture was stirred for 14 h then the DMF was removed under reduced pressure and the residue was partitioned between DCM and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel, eluting with ethyl acetate-cyclohexane (1:1 to 1:0) affording the title compound in 73% yield (1.772 g).

후처리

  1. customthe DMF was removed under reduced pressure
  2. customthe residue was partitioned between DCM and saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude compound was purified by flash chromatography on silica gel
  6. washeluting with ethyl acetate-cyclohexane (1:1 to 1:0)

출처 및 근거

ORD 기록
ord-339c975286c24749b1ddd0964fb968e4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732600B2

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