Nitrogen → 4-Chloro-2-[4-(4-dimethylamino-benzyl)-piperazin-1-yl]-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1172509Notes

Reaction equation

HRID 1172509 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:29])[C:8]2[O:14][C:13]3[C:15]([Cl:25])=[CH:16][C:17]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[CH:18][C:12]=3[CH2:11][S:10](=[O:27])(=[O:26])[C:9]=2[CH:28]=1)=[O:4].[CH3:30][N:31]([C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1C=O)[CH3:32].N#N.[C:43]([BH3-])#N.[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:29])[C:8]2[O:14][C:13]3[C:15]([Cl:25])=[CH:16][C:17]([N:19]4[CH2:20][CH2:21][N:22]([CH2:43][C:38]5[CH:37]=[CH:34][C:33]([N:31]([CH3:30])[CH3:32])=[CH:40][CH:39]=5)[CH2:23][CH2:24]4)=[CH:18][C:12]=3[CH2:11][S:10](=[O:26])(=[O:27])[C:9]=2[CH:28]=1)=[O:4]

Participants

8

Reactant 4

HCID 947NitrogenHCID 34289Benzaldehyde, (dimethylamino)-HCID 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 1317284794-Chloro-2-[4-(4-dimethylamino-benzyl)-piperazin-1-yl]-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Titanium isopropoxide (0.33 mL, 1.09 mmol) was added to a solution of Example 104k (0.4 g, 0.91 mmol) and dimethylaminobenzaldehyde (0.136 g, 0.91 mmol) in dry methanol (10 mL). The reaction mixture was stirred at 50° C. in an atmosphere of N2 for 1.5 h. It was cooled, treated with sodium cyanoborohydride (0.054 g, 0.86 mmol) and stirred for 1.5 h. It was then treated with cold water and extracted with n-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, MeOH/CHCl3) to obtain the title compound as a white solid. Yield: 0.275 g, (52.78%); 1H NMR (DMSO-d6): δ 2.7 (s, 3H, CH3), 3.00 (s, 6H, 2CH3), 3.20-3.25 (m, 4H, 2CH2), 3.55 (s, 4H, 2CH2), 3.95 (s, 3H, OCH3), 4.75 (s, 2H, CH2), 6.7-6.9 (m, 4H, Ar), 7.25 (s, 1H, Ar), 7.3 (s, 1H, Ar), 8.1 (s, 1H, Ar), 8.50 (s, 1H, Ar); MS: m/e (CI+) 570 (M+1).

Workup

  1. temperatureIt was cooled
  2. extractionextracted with n-butanol
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-9bef8ccf4e6041b8be29d4bda591529c
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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