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

HRID 1020256노트

반응식

HRID 1020256 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 580550601-(3-Fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea2회HCID 178499100HCID 178499100, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f86ec67000474d61ab5150d3d204eaad
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716320B2

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