Water → Methyl 3-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methoxy)pyrazine-2-carboxylate

HRID 1020256ノート

反応式

HRID 1020256 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15]I)[N:14]=1)=[O:8].[OH:20][C:21]1[C:22]([C:27]([O:29][CH3:30])=[O:28])=[N:23][CH:24]=[CH:25][N:26]=1.C([O-])([O-])=O.[K+].[K+].O>CN1CCCC1=O>[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7](=[O:8])[NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][O:20][C:21]2[C:22]([C:27]([O:29][CH3:30])=[O:28])=[N:23][CH:24]=[CH:25][N:26]=2)[N:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 580550601-(3-Fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea2 回HCID 178499100HCID 178499100、化合物

生成物 1

HCID 86622754Methyl 3-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methoxy)pyrazine-2-carboxylate

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

1-(3-fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea (Intermediate XXIII, 1.0 mmol) and methyl 3-hydroxypyrazine-2-carboxylate (1.0 mmol) were dissolved in N-methylpyrrolidinone (3 ml) and K2CO3 (1.1 eq) was added. The mixture was stirred overnight. 20 ml water was added and the product was extracted three times with dichloromethane. The organic was dried over Na2SO4, filtered, and concentrated. The crude was purified by column chromatography using 0-70% gradient of saturated ammonia/MeOH and dichloromethane. 1H NMR (400 MHz, DMSO-d6): 10.73 (s, 1H), 7.89 (d, 1H), 7.40 (d, 1H), 7.35 (m, 1H), 6.95-7.10 (m, 3H), 6.94 (m, 2H), 5.04 (s, 2H), 4.31 (d, 2H), 3.79 (s, 3H). MS (ES+): M/Z 418 (M+1).

後処理

  1. extractionthe product was extracted three times with dichloromethane
  2. dry with materialThe organic was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-f86ec67000474d61ab5150d3d204eaad
出典データセット
uspto-grants-2014_05
特許番号
US08716320B2

反応ノート

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