tert-Butanol → HCID 59013760、化合物

HRID 907556ノート

反応式

HRID 907556 の反応式
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27](Cl)=[N:26][CH:25]=[CH: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.CC(C)([O-])C.[K+].C(O)(C)(C)C.[Cl:42][C:43]1[CH:48]=[C:47]([CH2:49][OH:50])[CH:46]=[CH:45][N:44]=1>CO>[F:29][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([O:50][CH2:49][C:47]4[CH:46]=[CH:45][N:44]=[C:43]([Cl:42])[CH:48]=4)=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 7062237(2-Chloropyridin-4-yl)methanolHCID 23665647Potassium tert-butoxideHCID 59013946HCID 59013946、化合物

生成物 1

HCID 59013760HCID 59013760、化合物収率 21%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide (115 mg, 0.254 mmol) and 1M solution of potassium tert-butoxide in tert-butanol (0.80 mL, 0.80 mmol) was added 2-Chloro-4-pyridinemethanol (81.8 mg, 0.568 mmol). The resulting suspension was stirred at room temperature for 15 h. The crude reaction mixture was diluted with methanol and purified by preparative HPLC (50 mM NH4OAc(aq), Acetonitrile system). The product was isolated by lyophilization of pure fractions yielding N-[3,5-bis(trifluoromethyl)phenyl]-4-(3-{[(2-chloropyridin-4-yl)methyl]oxy}pyrazin-2-yl)piperazine-1-carboxamide (29.9 mg, 21% yield). 1H NMR (CDCl3) 8.41 (d, 1H), 7.91 (s, 2H), 7.82 (d, 1H), 7.61 (d, 1H), 7.54 (s, 1H), 7.39 (s, 1H), 6.70 (s, 1H), 5.47 (s, 2H), 3.70-3.65 (m, 8H) ppm.

後処理

  1. customThe crude reaction mixture
  2. custompurified by preparative HPLC (50 mM NH4OAc(aq), Acetonitrile system)
  3. customThe product was isolated by lyophilization of pure fractions

出典と根拠

ORDレコード
ord-b07c40a2d0f34e04a77d5f45db987fd8
出典データセット
uspto-grants-2011_09
特許番号
US08013156B2

反応ノート

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