Dimethylformamide → Ammonium Hydroxide

HRID 1661564ノート

反応式

HRID 1661564 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[C:6]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[C:5]2[CH3:26].[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+].CN(C=[O:37])C>>[NH4+:7].[OH-:37].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]3[N:27]=[N:28][NH:29][N:17]=3)=[CH:18][CH:19]=1)[C:6]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[C:5]2[CH3:26]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 582156974-(5-chloro-3-methyl-2-pyridin-3-yl-1H-indol-1-ylmethyl)-benzonitrile

生成物 2

HCID 14923Ammonium Hydroxide収率 0.1%HCID 582157675-chloro-3-methyl-2-pyridin-3-yl-1-[4-(2H-tetrazol-5-yl)-benzyl]-1H-indole

反応条件

温度
120 °C

実験手順

To a solution of 4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzonitrile (Example 17, 179 mg, 0.5 mmol) in DMF (5 mL) is added sodium azide (97 mg, 1.5 mmol) and ammonium chloride (80 mg, 1.5 mmol) and the mixture is heated to 120° C. The reaction mixture is cooled to room temperature and filtered. The filtrate is purified by reverse phase HPLC with Xbridge C18 and a gradient of 0.1% NH4OH in acetonitrile to give 5-chloro-3-methyl-2-pyridin-3-yl-1-[4-(2H-tetrazol-5-yl)-benzyl]-1H-indole. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.21 (s, 3H), 5.34 (s, 2H), 6.81 (d, J=8.1 Hz, 2H), 7.11 (br. s, 1H), 7.17 (dd, J=8.7, 2.1 Hz, 1H), 7.48-7.53 (m, 2H), 7.67 (d, J=2.0 Hz, 1H), 7.77 (d, J=8.3 Hz, 2H), 7.80-7.84 (m, 1H), 8.60 (d, J=1.5 Hz, 1H), 8.62 (dd, J=4.8, 1.5 Hz, 1H). HRMS (ESI) m/z 401.1276 [(M+H)+ Calcd for C22H18N6Cl: 401.1281].

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate is purified by reverse phase HPLC with Xbridge C18

出典と根拠

ORDレコード
ord-3382b042dff947abbfa21f1db49e00b0
出典データセット
uspto-grants-2011_10
特許番号
US08030334B2

反応ノート

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