Trifluoroacetic acid → 1-(2,5-Dichloro-pyrimidin-4-yl)-piperidine-4-carboxylic acid [1-(3-chloro-phenyl)-2-hydroxy-ethyl]-amide

HRID 1295675ノート

反応式

HRID 1295675 の反応式
C(OC(N1CCN([C:14](=[O:26])[NH:15][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH2:17][OH:18])CC1)=O)(C)(C)C.F[C:28](F)(F)[C:29](O)=O.[Cl:34][C:35]1[N:40]=[C:39](Cl)[C:38]([Cl:42])=[CH:37][N:36]=1>C(Cl)Cl>[Cl:25][C:21]1[CH:20]=[C:19]([CH:16]([NH:15][C:14]([CH:29]2[CH2:28][CH2:14][N:15]([C:39]3[C:38]([Cl:42])=[CH:37][N:36]=[C:35]([Cl:34])[N:40]=3)[CH2:16][CH2:17]2)=[O:26])[CH2:17][OH:18])[CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 2372592,4,5-TrichloropyrimidineHCID 694145564-[1-(3-Chloro-phenyl)-2-hydroxy-ethylcarbamoyl]-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 866013611-(2,5-Dichloro-pyrimidin-4-yl)-piperidine-4-carboxylic acid [1-(3-chloro-phenyl)-2-hydroxy-ethyl]-amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-[1 -(3-Chloro-phenyl)-2-hydroxy-ethylcarbamoyl]-piperazine- 1-carboxylic acid tert-butyl ester was deprotected with 10% trifluoroacetic acid in methylene chloride by stirring overnight at ambient temperature. The reaction was concentrated in vacuo and the resulting TFA salt was dissolved in DMF (1 mL) and DIEA (0.25 mL). This mixture was heated with 2,4,5-trichloropyrimidine (52 mg. 0.28 mmol) at 80° C. for 18 hours. Purification by prep HPLC (Gilson: Column=CombiHT SB-C189 5 μM 21.2 mm×100 mm, eluent=0.1% TFA MeCN/H2O gradient) afforded the title compound as a yellow oil (47 mg) Rt=5.97 minutes; MS FIA 429.9 (M+1).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe resulting TFA salt was dissolved in DMF (1 mL)
  3. customPurification by prep HPLC (Gilson: Column=CombiHT SB-C189 5 μM 21.2 mm×100 mm, eluent=0.1% TFA MeCN/H2O gradient)

出典と根拠

ORDレコード
ord-0cd86aae0bcc488387d5491d8850ab71
出典データセット
uspto-grants-2007_07
特許番号
US07244735B2

反応ノート

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