Triethylamine → 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (1-methanesulfonyl-piperidin-3-ylmethyl)-amide

HRID 219681ノート

反応式

HRID 219681 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[NH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][NH:14][C:15]([C:17]2[CH:18]=[N:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[N:21][CH:22]=2)=[O:16])[CH2:8]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][NH:14][C:15]([C:17]2[CH:22]=[N:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[N:19][CH:18]=2)=[O:16])[CH2:8]1)(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866232202-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (piperidin-3-ylmethyl)-amide hydrochloride

生成物 1

HCID 166660982-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (1-methanesulfonyl-piperidin-3-ylmethyl)-amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Methanesulfonyl chloride (0.523 mmol) is added to a stirred solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (piperidin-3-ylmethyl)-amide hydrochloride (0.523 mmol) and triethylamine (2.62 mmol) in DCM (20 mL) at 0° C. The mixture is stirred at 0° C. for an hour, and then stirred at room temperature overnight. The reaction mixture is washed with water (20 mL). The organic layer is separated, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with EtOAc to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (1-methanesulfonyl-piperidin-3-ylmethyl)-amide as a solid. MS: 393 (M+H); 1H NMR (300 MHz, CD3OD): δ 1.43-1.95 (m, 4H), 2.10-2.23 bs, H), 3.04-3.50 (m, 5H), 3.60-3.78 (m, H), 6.71-6.90 (bs, N—H), 7.18-7.23 (m, H), 7.42-7.57 (m, H), 8.18-8.37 (q, 2H), 9.20 (s, 2H).

後処理

  1. stirringstirred at room temperature overnight
  2. washThe reaction mixture is washed with water (20 mL)
  3. customThe organic layer is separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel column chromatography
  8. washeluting with EtOAc

出典と根拠

ORDレコード
ord-872f1eb5915f4e0fb9f3964213213ceb
出典データセット
uspto-grants-2012_06
特許番号
US08202863B2

反応ノート

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