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

HRID 1020256Notes

Reaction equation

HRID 1020256 reaction equation
[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

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 580550601-(3-Fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea2×HCID 178499100HCID 178499100, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f86ec67000474d61ab5150d3d204eaad
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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