Chlorotrimethylsilane → 6-cyano-2-(2-(4-ethyl-3-(4-morpholinopiperidin-1-yl)phenyl)propan-2-yl)-1H-indole-3-carboxylic acid

HRID 61875

반응식

HRID 61875 반응식
Cl.C([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[C:8]([C:17]([OH:19])=[O:18])=[C:7]1[C:20]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH3:30])=[C:25]([N:31]2[CH2:36][CH2:35][CH:34]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH2:33][CH2:32]2)[CH:24]=1)([CH3:22])[CH3:21])(C)(C)C.C[Si](Cl)(C)C.[OH-].[Na+].OP([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:15]([C:12]1[CH:13]=[C:14]2[C:9]([C:8]([C:17]([OH:19])=[O:18])=[C:7]([C:20]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH3:30])=[C:25]([N:31]4[CH2:32][CH2:33][CH:34]([N:37]5[CH2:38][CH2:39][O:40][CH2:41][CH2:42]5)[CH2:35][CH2:36]4)[CH:24]=3)([CH3:22])[CH3:21])[NH:6]2)=[CH:10][CH:11]=1)#[N:16]

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 24450Potassium Phosphate, DibasicHCID 66835223Tert-butyl 6-cyano-2-(2-(4-ethyl-3-(4-morpholin-4-yl-piperidin-1-yl)phenyl)propan-2-yl)-1H-indole-3-carboxylic acid hydrochloric acid salt

생성물 1

HCID 668352186-cyano-2-(2-(4-ethyl-3-(4-morpholinopiperidin-1-yl)phenyl)propan-2-yl)-1H-indole-3-carboxylic acid수율 96.6%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Tert-butyl 6-cyano-2-(2-(4-ethyl-3-(4-morpholin-4-yl-piperidin-1-yl)phenyl)propan-2-yl)-1H-indole-3-carboxylic acid hydrochloric acid salt (1400 g) was suspended in TFE (7 L) under nitrogen stream, and added dropwise with TMSCl (554 ml) at 8° C. After stirring for 3 hrs, the reaction solution was added with acetone (5.6 L) and aqueous solution of NaOH (1 N, 4.39 L), and 10% aqueous solution of K2HPO4 (1.4 L) was added thereto for neutralization. The precipitated solid was filtered and collected, washed twice with a mixture solution of water:acetone (=1:1, 2.8 L), and dried to obtain the title compound (1061 g, 96.6%).

후처리

  1. additionwas added
  2. filtrationThe precipitated solid was filtered
  3. customcollected
  4. washwashed twice with a mixture solution of water
  5. dry with materialacetone (=1:1, 2.8 L), and dried

출처 및 근거

ORD 기록
ord-4b4881646c254cb996144fcd8ef36721
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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