Hydrochloric Acid → HCID 58387878, compound

HRID 2080217Notes

Reaction equation

HRID 2080217 reaction equation
C(O[C:6](=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:30])[NH:15][CH2:16][C:17]2[S:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[CH:20][CH:21]=2)=[CH:10][N:9]=1)(C)(C)C.NC1N=C(N)C=CC=1C(NCC1SC(CC2SC3C=CC=CC=3C=2)=CC=1)=O.[CH3:59][O:60][CH2:61]CBr.[H-].[Na+].Cl>CS(C)=O.C(OCC)(=O)C.O>[F:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[O:22][C:19]1[S:18][C:17]([CH2:16][NH:15][C:14](=[O:30])[C:11]2[CH:12]=[CH:13][C:8]([NH:7][CH2:6][CH2:59][O:60][CH3:61])=[N:9][CH:10]=2)=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 58387881HCID 58387881, compoundHCID 67119683HCID 67119683, compound

Product 1

HCID 58387878HCID 58387878, compoundYield 42.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of (5-((5-(3-fluoro-phenoxy)-thiophen-2-ylmethyl)-carbamoyl)-pyridin-2-yl)-carbamic acid tert-butyl ester described in Preparation Example A+−2 (100 mg, 0.227 mmol) and methoxyethyl bromide (38 mg, 0.272 mmol) in dimethylsulfoxide (5 mL) was added sodium hydride (11 mg, 0.272 mmol, 60% in oil), and the solution was stirred at room temperature for 1 hour. 5N Hydrochloric acid was added to the reaction solution, which was then stirred for 5 minutes at 80° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with water twice, then, silica gel was added, the solvent was evaporated in vacuo for adsorption, purification was carried out by silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate), and the title compound (39 mg, 0.097 mmol, 42.8%) was obtained as a white solid.

Workup

  1. stirringwas then stirred for 5 minutes at 80° C
  2. customwas then partitioned
  3. washthe organic layer was washed with water twice
  4. additionsilica gel was added
  5. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-d5d81444cecf4059b69d055b0b0efc40
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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