Tetrahydrofuran → HCID 23502792, compound

HRID 1835342Notes

Reaction equation

HRID 1835342 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[CH:33]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])[C:12]([C:13]([N:15]([CH2:17][C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=3)[CH3:16])=[O:14])=[CH:11][N:10]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O1CCCC1>C(O)C>[F:31][C:28]([F:29])([F:30])[C:20]1[CH:19]=[C:18]([CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=1)[CH2:17][N:15]([CH3:16])[C:13](=[O:14])[C:12]1[C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])=[CH:33][C:9]([C:7]2[S:8][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][CH:6]=2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 10303579HCID 10303579, compound

Product 1

HCID 23502792HCID 23502792, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 50 mg (0.087 mmol) 6-(5-acetyl-thiophen-2-yl)-N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-4-o-tolyl-nicotinamide (Example 38), 7 mg (0.2 mmol) sodium borohydride in 1 ml ethanol and a small amount of tetrahydrofuran was stirred at room temperature for 2 h. The reaction was quenched by addition of water, followed by 1 N aqueous hydrochloric acid solution. The mixture was basified with sodium carbonate and extracted with 3 portions of ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered and concentrated to give 48 mg (96%) of the title compound as a slightly yellow solid.

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionextracted with 3 portions of ethyl acetate
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4ecad0ef3c93400c96f2f165c9fa85b2
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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