tert-Butanol → HCID 59013877, 화합물

HRID 907544

반응식

HRID 907544 반응식
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:26](Cl)=[N:25][S:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:30][N:31]([CH3:40])[C:32]1[CH:33]=[C:34]([CH2:38][OH:39])[CH:35]=[CH:36][CH:37]=1.C(C(CCC)[O-])(C)(C)C.[K+].C(O)(C)(C)C>>[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:26]([O:39][CH2:38][C:34]4[CH:35]=[CH:36][CH:37]=[C:32]([N:31]([CH3:40])[CH3:30])[CH:33]=4)=[N:25][S:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

참가 물질

5

반응물 4

HCID 6386tert-ButanolHCID 90133m-(Dimethylamino)benzyl alcoholHCID 23710422Potassium tert-butylbutoxideHCID 59013796HCID 59013796, 화합물

생성물 1

HCID 59013877HCID 59013877, 화합물수율 55%

실험 절차

To a round bottom flask equipped with a magnetic stir bar was added 4-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide (0.1 g, 0.21 mmol, 1.0 eq.), (3-Dimethylamino-phenyl)-methanol (0.065 g, 0.062 mL, 0.43 mmol, 2.0 eq) and 1M potassium tert-butyl butoxide in t-butanol (0.65 ml, 0.65 mmol, 3.0 eq). The mixture was stirred at room temperature overnight. After removal of solvent in vacuo, the crude mixture was purified on preparative HPLC, affording the title compound N-[3,5-bis(trifluoromethyl)phenyl]-4-[4-({[3-(dimethylamino)phenyl]methyl}oxy)-1,2,5-thiadiazol-3-yl]piperazine-1-carboxamide as a white solid (0.06 g, 55% yield). 1H NMR (DMSO-d6) 9.23 (s, 1H), 8.18 (s, 2H), 7.59 (s, 1H), 7.22 (m, 1H), 6.89 (s, 1H), 6.78 (m, 2H), 5.39 (m, 4H), 3.61 (m, 4H), 3.53 (m, 4H), 2.92 (s, 6H) ppm.

후처리

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customAfter removal of solvent in vacuo
  3. customthe crude mixture was purified on preparative HPLC

출처 및 근거

ORD 기록
ord-4dba1c719cd946d5a16932574d7689b4
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013156B2

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