Water → 1-(3-Fluorobenzyl)-3-(4-((3-methylpyrazin-2-yloxy)methyl)thiazol-2-yl)urea

HRID 1020257Notes

Reaction equation

HRID 1020257 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].[Na].[CH3:21][C:22]1[C:23]([OH:28])=[N:24][CH:25]=[CH:26][N:27]=1.O>CN(C)C=O>[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][O:28][C:23]2[C:22]([CH3:21])=[N:27][CH:26]=[CH:25][N:24]=2)[N:14]=1)=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 580550601-(3-Fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)ureaHCID 178432941HCID 178432941, compound

Product 1

HCID 250515261-(3-Fluorobenzyl)-3-(4-((3-methylpyrazin-2-yloxy)methyl)thiazol-2-yl)urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea (1.0 mmol) and excess of 3-methylpyrazin-2-ol sodium salt were dissolved in N,N-dimethylformamide (3 ml). The mixture was stirred overnight. Water (20 ml) 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), 7.48 (d, 1H), 7.36 (m, 1H), 7.15 (d, 1H), 7.06-7.12 (m, 3H), 6.96)m, 1H), 6.89 (s, 1H), 4.99 (s, 2H), 4.33 (d, 2H), 2.28 (s, 3H). MS (ES+): M/Z 374 (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-3680288cc1c246dea62e1521bb7ff5d9
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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