tert-Butanol → HCID 59013877、化合物

HRID 907544

反応式

HRID 907544 の反応式
[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

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 90133m-(Dimethylamino)benzyl alcoholHCID 23710422Potassium tert-butylbutoxideHCID 59013796HCID 59013796、化合物

生成物 1

HCID 59013877HCID 59013877、化合物収率 55%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4dba1c719cd946d5a16932574d7689b4
出典データセット
uspto-grants-2011_09
特許番号
US08013156B2

関連ノート

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