Acetic Acid → HCID 86758931, compound

HRID 1267131Notes

Reaction equation

HRID 1267131 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[C:17]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[NH:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[CH:38]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[NH:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[CH2:38][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[C:17]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:32])[F:31])=[CH:25][CH:24]=4)=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 13854Pyrrole-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11166547HCID 11166547, compound

Product 1

HCID 86758931HCID 86758931, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-methyl-4′-trifluoromethyl-biphenyl-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amide (329 mg) in 1,2-dichloroethane (20 mL) was added 1H-pyrrole-2-carboxaldehyde (86 mg) and acetic acid (54 mg). The solution was cooled at 0° C. and sodium triacetoxy borohydride (238 mg) was added portionwise and the mixture was stirred at room temperature for 16 hours. The solution was then washed with a saturated solution of NaHCO3, with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with CH2Cl2/MeOH (95/5) and the oily residue obtained was crystallized from diisopropyl ether to give the title compound (210 mg) as white crystals.

Workup

  1. washThe solution was then washed with a saturated solution of NaHCO3, with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. washeluting with CH2Cl2/MeOH (95/5)
  7. customthe oily residue obtained
  8. customwas crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-9190c26f6f87433db2827987cea57521
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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