Hydrochloric Acid → HCID 23130805, compound

HRID 2080221Notes

Reaction equation

HRID 2080221 reaction equation
Cl.C(OC(=O)NC[C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:32])[NH:17][CH2:18][C:19]2[S:20][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)=[CH:22][CH:23]=2)=[CH:12][N:11]=1)(C)(C)C.[NH2:34][C:35]1C(C(O)=O)=NC=C(N)N=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(O)C>[F:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[O:24][C:21]1[S:20][C:19]([CH2:18][NH:17][C:16](=[O:32])[C:13]2[CH:14]=[CH:15][C:10]([NH:34][CH3:35])=[N:11][CH:12]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21548009HCID 21548009, compoundHCID 67119688HCID 67119688, compound

Product 1

HCID 23130805HCID 23130805, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Ethanol (20 mL) and 5N hydrochloric acid (0.8 mL) were added to (5-((5-(3-fluoro-phenoxy)-thiophen-2-ylmethyl)carbamoyl)pyridin-2-yl)methyl-carbamic acid tert-butyl ester described in Preparation Example A+-3 (87 mg, 0.19 mmol), and the solution was stirred for 25 minutes at 80° C. An aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with water twice, washed with brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, and the title compound (58 mg, 0.162 mmol, 85.5%) was obtained as a white solid.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed with water twice
  3. washwashed with brine
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d62c413c88904a5c87f67f9706507654
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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