4-(Trifluoromethyl)benzaldehyde → HCID 131728484, compound

HRID 1172514Notes

Reaction equation

HRID 1172514 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:13][O:14][C:15]([C:17]1[CH:18]=[C:19]([CH3:41])[C:20]2[O:26][C:25]3[C:27]([Cl:37])=[CH:28][C:29]([N:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:30][C:24]=3[CH2:23][S:22](=[O:39])(=[O:38])[C:21]=2[CH:40]=1)=[O:16].C([BH3-])#N.[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:13][O:14][C:15]([C:17]1[CH:18]=[C:19]([CH3:41])[C:20]2[O:26][C:25]3[C:27]([Cl:37])=[CH:28][C:29]([N:31]4[CH2:32][CH2:33][N:34]([CH2:7][C:6]5[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=5)[CH2:35][CH2:36]4)=[CH:30][C:24]=3[CH2:23][S:22](=[O:38])(=[O:39])[C:21]=2[CH:40]=1)=[O:16]

Participants

6

Reactant 3

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 115410724-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

Product 1

HCID 131728484HCID 131728484, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

p-(Trifluoromethyl)benzaldehyde (0.119 g, 0.687 mmol) and titanium isopropoxide (0.26 mL, 0.858 mmol) were added to a suspension of Example 104k (0.3 g, 0.687 mmol) in methanol (30 mL). The reaction mixture was refluxed for 1.5 h, cooled to room temperature, treated with sodium cyanoborohydride (0.042 g, 0.66 mmol) and stirred for 3 h. It was concentrated, treated with water and extracted with n-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 20% ethyl acetate/pet ether) to obtain the title compound. Yield: 0.12 g, (28.7%); 1H NMR (DMSO-d6): δ 2.6 (h, 4H, 2CH2), 2.7 (s, 3H, CH3), 3.2 (h, 4H, 2CH2), 3.6 (s, 2H, CH2), 3.9 (s, 3H, OCH3), 4.6 (s, 2H, CH2), 6.7 (s, H, Ar), 6.9 (s, 1H, Ar), 7.5 (d, 2H, Ar), 7.6 (d, 2H, Ar), 8.1 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (ES+) 596 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 h
  2. concentrationIt was concentrated
  3. additiontreated with water
  4. extractionextracted with n-butanol
  5. washThe organic layer was washed with water, brine
  6. customdried
  7. concentrationconcentrated
  8. custompurified

Sources & evidence

ORD record
ord-3d1d65af1c5947ceb155f10c3488a446
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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