Ammonium Chloride → 3-Chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-indazol-4-yl]oxy}benzonitrile

HRID 505510ノート

反応式

HRID 505510 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)[CH:9]=1)[C:5]#[N:6].CC(C)([O-])C.[Li+].Cl[CH2:28][C:29]1[C:37]2[C:32](=[N:33][C:34]([NH:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)=[CH:35][CH:36]=2)[N:31]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[N:30]=1.[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][N:15]3[CH2:28][C:29]2[C:37]3[C:32](=[N:33][C:34]([NH:38][CH2:39][C:40]4[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=4)=[CH:35][CH:36]=3)[N:31]([CH2:48][C:49]3[CH:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=3)[N:30]=2)[CH:9]=1)[C:5]#[N:6]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 568336433-chloro-5-[(5-chloro-1H-indazol-4-yl)oxy]benzonitrileHCID 568336463-(Chloromethyl)-N,1-bis(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amine2 回

生成物 1

HCID 568338523-Chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-indazol-4-yl]oxy}benzonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

3-chloro-5-[(5-chloro-1H-indazol-4-yl)oxy]benzonitrile (0.677 g, 2.225 mmol) and lithium tert-butoxide (0.178 g, 2.225 mmol) were dissolved in DMF (5 μL) and allowed to stir for 5 minutes. To this mixture at 0° C. was added 3-(chloromethyl)-N,1-bis(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amine (Intermediate 2; 0.896 g, 2.119 mmol) as a solution in DMF (5 mL). The mixture was then allowed to warm to room temperature overnight, after which aqueous ammonium chloride (20 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with water (5×50 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was subjected to automated silica gel chromatography eluting with a gradient of 0-10% ethyl acetate in dichloromethane to yield the title product. LRMS (M+1)=691.8

後処理

  1. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  2. washThe combined organic fractions were washed with water (5×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washeluting with a gradient of 0-10% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-bfebf9f342294e6db107179e9ca3dec6
出典データセット
uspto-grants-2010_08
特許番号
US07781454B2

反応ノート

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