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 472530노트

반응식

HRID 472530 반응식
[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]

참가 물질

7

반응물 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

생성물 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]-amine수율 49%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-8ee77b84be1a428ba3240477f1bec2ec
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633173B2

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