Diisopropylethylamine → N-({3-[(3-butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

HRID 1875165노트

반응식

HRID 1875165 반응식
[CH2:1]([C:5]1[CH:6]=[C:7]([O:12][C:13]2[C:14]([F:22])=[C:15]([CH2:20][NH2:21])[CH:16]=[CH:17][C:18]=2[Cl:19])[CH:8]=[C:9]([Cl:11])[CH:10]=1)[CH2:2][CH2:3][CH3:4].[Cl:23][C:24]1[N:25]=[CH:26][N:27]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:28]=1[C:29](O)=[O:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:5]1[CH:6]=[C:7]([O:12][C:13]2[C:14]([F:22])=[C:15]([CH2:20][NH:21][C:29]([C:28]3[N:27]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])[CH:26]=[N:25][C:24]=3[Cl:23])=[O:30])[CH:16]=[CH:17][C:18]=2[Cl:19])[CH:8]=[C:9]([Cl:11])[CH:10]=1)[CH2:2][CH2:3][CH3:4]

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 68485437({3-[(3-Butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amineHCID 684855334-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid

생성물 1

HCID 68483744N-({3-[(3-butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide수율 82%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of ({3-[(3-butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine (105 mg, 0.307 mmol), 4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (85 mg, 0.307 mmol) and HATU (117 mg, 0.307 mmol) in DMF (3 ml) was added diisopropylethyl amine (0.107 ml, 0.614 mmol) and the reaction mixture was stirred at rt for 45 minutes. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give N-({3-[(3-butyl-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (151 mg, 0.251 mmol, 82% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.73 (t, 1H), 7.95 (s, 1H), 7.39-7.46 (m, 1H), 7.34 (t, 1H), 6.99 (s, 1H), 6.70 (s, 1H), 6.66 (s, 1H), 5.47 (s, 2H), 4.45 (d, 2H), 3.36 (t, 2H), 2.50 (t, 2H), 1.46 (t, 2H), 1.16-1.28 (m, 2H), 0.82 (t, 3 H), 0.73 (t, 2H), −0.12 (s, 9H).

후처리

  1. washwashed with water
  2. customThe solvent was removed
  3. customthe crude material was purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-c2cc08273ddd40869218871c372b4c52
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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