1,2-Dichloroethane → N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxamide

HRID 1025405ノート

反応式

HRID 1025405 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:23])=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([C:20](O)=[O:21])[CH2:16][CH2:15]3)[N:12]=2)=[CH:4][CH:3]=1.[N:24]1([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C>[N:24]1([CH2:31][CH2:32][CH2:33][NH:34][C:20]([CH:17]2[CH2:16][CH2:15][N:14]([CH2:13][C:11]3[N:12]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[O:9][C:10]=3[CH3:23])[CH2:19][CH2:18]2)=[O:21])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 27643953-(Azepan-1-yl)propan-1-amineHCID 209671331-((2-(4-Chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

生成物 1

HCID 20859820N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxamide収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid (0.25 g, 0.75 mmole), 3-(Azepan-1-yl)propan-1-amine (0.33 g) and DIPEA (0.32 mL) in DMF (5 mL) was added EDC (0.153 g). The reaction solution was stirred at room temperature overnight. The solvent removed and EtOAc (100 mL) was added. The organic layer was washed with saturated sodium bicarbonate (50 mL), water (50 mL) and dried over anhydrous magnesium sulfate. After filtration, the residue after concentration of the filtrate was crystallized from EtOAc/Hexane to provide the N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxamide as white solid (0.30 g, 85%). H1NMR (300 MHz, CDCl3), ppm: 7.94 (d, 2H), 7.49 (m, 1H), 7.39 (d, 2H), 3.44 (s, 2H), 3.36 (m, 2H), 2.99 (d, 2H), 2.67 (m, 4H), 2.60 (t, 2H), 2.39 (s, 3H), 2.07 (m, 3H), 1.83 (m, 4H), 1.65 (m, 10H). MS (ESI+) M/z: 473, 475 (M+H).

後処理

  1. customThe solvent removed
  2. additionEtOAc (100 mL) was added
  3. washThe organic layer was washed with saturated sodium bicarbonate (50 mL), water (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe residue after concentration of the filtrate was crystallized from EtOAc/Hexane

出典と根拠

ORDレコード
ord-d2325b91b2ba4bbea4252a52d684c21e
出典データセット
uspto-grants-2014_05
特許番号
US08729081B2

反応ノート

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