Hydrochloric Acid → HCID 22267292, compound

HRID 488873Notes

Reaction equation

HRID 488873 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[C:13]([CH2:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[C:25]([F:28])([F:27])[F:26])=[O:16])=[C:12]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:11]2[C:6](=[CH:7][C:8]3[C:37](=[O:38])[CH2:36][CH2:35][C:9]=3[CH:10]=2)[O:5]1.CO.Cl>COCCOC>[F:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[CH2:14][C:13]2[C:4](=[O:3])[O:5][C:6]3[C:11]([C:12]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:10][C:9]2[CH2:35][CH2:36][CH:37]([OH:38])[C:8]=2[CH:7]=3)=[C:19]([C:25]([F:28])([F:26])[F:27])[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 22267281HCID 22267281, compound

Product 1

HCID 22267292HCID 22267292, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of NaBH4 (30 mg) in DME (2 ml) was combined with 2-(2,8-dioxo-4-phenyl-2,6,7,8-tetrahydrocyclopenta[g]chromen-3-yl)-N-[4-fluoro-2-(trifluoromethyl)phenyl]-acetamide (Example 88) (170 mg) with cooling in ice, and further combined with methanol, and stirred at room temperature for 10 minutes. The reaction solution was poured into diluted hydrochloric acid, which was then extracted with ethyl acetate. The extract was washed with water, and then dried over magnesium sulfate, and concentrated under reduced pressure to obtain the title compound as a colorless crystal (110 mg, yield: 65%). An aliquot was recrystallized from ethyl acetate to measure a melting point. Melting point: 217-218° C.

Workup

  1. temperaturewith cooling in ice
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee738e502d344d4aa1cada766821fb44
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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