Sodium Iodide → [3-(2-Methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl]-[5-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine

HRID 472530ノート

反応式

HRID 472530 の反応式
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]2[N:16]=[C:17]([NH:19][C:20]3[CH:30]=[CH:29][C:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28][C:22]=4[CH:21]=3)[N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:38][CH2:39][S:40]([CH3:43])(=[O:42])=[O:41].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:43][S:40]([CH2:39][CH2:38][N:26]1[CH2:27][CH2:28][C:22]2[CH:21]=[C:20]([NH:19][C:17]3[N:18]=[C:14]4[CH:13]=[CH:12][CH:11]=[C:10]([C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[CH2:3][O:2][CH3:1])[N:15]4[N:16]=3)[CH:30]=[CH:29][C:23]=2[CH2:24][CH2:25]1)(=[O:42])=[O:41]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 3035331-Chloro-2-methanesulfonylethaneHCID 59612550[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amine

生成物 1

HCID 59612426[3-(2-Methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl]-[5-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine収率 49%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of [5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine (0.100 g, 0.250 mmol) in N,N-dimethylformamide (3 mL) was added potassium carbonate (0.103 g, 0.751 mmol), 1-chloro-2-methanesulfonyl-ethane (0.053545 g, 0.37548 mmol), followed by sodium iodide (0.037 g, 0.250 mmol) and the reaction was heated at 60° C. overnight then cooled to room temperature. The reaction was diluted with ethyl acetate, washed with water several times, washed with brine, dried over sodium sulfate, and concentrated. Product was isolated as a pale yellow foam (0.062 g, 49%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.64 (d, J=7.7 Hz, 1H), 7.59-7.42 (m, 5H), 7.31-7.29 (m, 1H), 7.24-7.20 (m, 1H), 7.08 (s, 1H), 6.98 (d, J=8.1 Hz, 1H), 6.92-6.88 (m, 1H), 4.35 (br s, 2H), 3.20-3.14 (m, 5H), 3.06 (s, 3H), 3.01 (t, J=6.1 Hz, 2H), 2.87-2.82 (m, 4H), 2.71-2.64 (m, 4H). MS=506 (MH)+.

後処理

  1. temperaturethen cooled to room temperature
  2. washwashed with water several times
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8ee77b84be1a428ba3240477f1bec2ec
出典データセット
uspto-grants-2014_01
特許番号
US08633173B2

反応ノート

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