Diisopropylethylamine → (R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide

HRID 85175

반응식

HRID 85175 반응식
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18](O)=[O:19])[C:11]=2[N:10]=1.[CH3:23][C:24]1([CH3:38])[O:28][C@H:27]([CH2:29][O:30][C:31]2[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=2)[NH2:34])[CH2:26][O:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[CH3:23][C:24]1([CH3:38])[O:28][C@H:27]([CH2:29][O:30][C:31]2[CH:32]=[C:33]([NH:34][C:18]([C:17]3[C:11]4[N:10]=[C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[C:2]([F:1])([F:21])[F:22])[NH:13][C:12]=4[CH:14]=[CH:15][CH:16]=3)=[O:19])[CH:35]=[CH:36][CH:37]=2)[CH2:26][O:25]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58552948HCID 58552948, 화합물HCID 672016022-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

생성물 1

HCID 67203479(R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

2-(2-(Trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (3; 75 mg, 0.24 mmol) was taken up in NMP (2 mL) along with (R)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)aniline (133; 64.3 mg, 0.288 mmol) and HATU (186 mg, 0.49 mmol). DIEA (81 μL, 0.49 mmol) was added and the resulting reaction mixture was stirred at room temperature for 12 h. The temperature was then raised to 60° C. and the reaction mixture was allowed to stir for an additional 1 h. The reaction mixture was diluted with water and filtered. The collected solids were further purified by silica gel chromatography to afford the desired product 134, as a yellow solid (51.5 mg, 42%).

후처리

  1. customthe resulting reaction mixture
  2. temperatureThe temperature was then raised to 60° C.
  3. stirringto stir for an additional 1 h
  4. filtrationfiltered
  5. customThe collected solids were further purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-930a91f7a1494d79b2bed38bf4945ef7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846947B2

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