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

HRID 15860

反応式

HRID 15860 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-339c975286c24749b1ddd0964fb968e4
出典データセット
uspto-grants-2010_06
特許番号
US07732600B2

関連ノート

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