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Dimethyl Sulfoxide → Telmisartan

HRID 2363803
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HRID 2363803 반응식
[CH3:1][CH2:2][CH2:3][C:4]1[NH:12][C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]3[N:21]([CH3:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH:10]=2)[N:5]=1.[CH3:24]S(C)=O.[OH-].[Na+].C[O:31][C:32]([C:34]1[C:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:36][CH:37]=[C:38](CBr)[CH:39]=1)=[O:33]>CC(C)=O.ClCCl.C(O)(=O)C.O>[CH2:3]([C:4]1[N:12]([CH2:24][C:45]2[CH:44]=[CH:43][C:42]([C:35]3[C:34]([C:32]([OH:31])=[O:33])=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:47][CH:46]=2)[C:11]2[CH:10]=[C:9]([C:13]3[N:21]([CH3:22])[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N:14]=3)[CH:8]=[C:7]([CH3:23])[C:6]=2[N:5]=1)[CH2:2][CH3:1]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 97964884-Methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazoleHCID 19595328Methyl 4-(bromomethyl)(1,1'-biphenyl)-2-carboxylate

생성물 1

HCID 65999Telmisartan수율 80%

시약·촉매·용매 4

HCID 176
Acetic Acid
용매
HCID 180Acetone용매
HCID 962Water용매
HCID 6344Dichloromethane용매

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온도
27.5 °C

실험 절차

50 gm of [1H-Benzimidazole-2-n-propyl-4-methyl-6-(1′-methyl benzimidazole-2′-yl)] was added to 200 ml dimethyl sulfoxide and 50 gm of sodium hydroxide. To this was added 60 gm of methyl-4-(bromomethyl)biphenyl-2-carboxylate at ambient temperature. The contents were stirred for 2 hours at 25-30° C. and then heated to 40-50 and maintained for 2 hours. About 500 ml water was added to the reaction mixture and acidified with acetic acid to pH 4.2, extract4ed twice with 250 ml of dichloromethane and the combined extracts were concentrated and isolated by filtration after addition of 300 ml acetone, dried under reduced pressure at 50-60° C. to give 75.0 gm (80%) of the title compound.

후처리

  1. temperatureheated to 40-50
  2. temperaturemaintained for 2 hours
  3. concentrationthe combined extracts were concentrated
  4. customisolated by filtration
  5. customdried under reduced pressure at 50-60° C.

출처 및 근거

ORD 기록
ord-99c70cc063544aa992b7306435a3c593
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691999B2

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