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

HRID 1927499Notes

Reaction equation

HRID 1927499 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][C:31]1[O:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1.C([BH3-])#N.[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[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]([CH2:35][C:34]5[O:37][C:31]([CH3:30])=[CH:32][CH:33]=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

6

Reactant 3

HCID 120975-MethylfurfuralHCID 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 1317284814-Chloro-6-methyl-2-[4-(5-methyl-furan-2-ylmethyl)-piperazin-1-yl]-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

Titanium isopropoxide (0.085 mL, 0.28 mmol) was added to a solution of Example 104k (0.1 g, 0.22 mmol) and 5-methyl furfuraldehyde (0.115 mL, 1.14 mmol) in dry methanol (10 mL). The reaction mixture was processed as described in the synthesis of Example 108k using sodium cyanoborohydride (0.013 g, 0.21 mmol) to obtain the title compound. Yield: 0.085 g, (70%); 1H NMR (CDCl3): δ 2.3 (s, 3H, CH3), 2.6 (t, 4H, 2CH2), 2.7 (s, 3H, CH3), 3.24 (t, 4H, 2CH2), 3.55 (s, 2H, CH2), 3.91 (s, 3H, OCH3), 4.63 (s, 2H, CH2), 5.9 (d, 1H, Ar), 6.1 (d, 1H, Ar), 6.76 (d, 1H, Ar), 6.88 (s, 1H, Ar), 8.06 (s, 1H, Ar), 8.44 (d, 1H, Ar); MS: m/e (EI+) 532 (M+1).

Workup

  1. customas described in the synthesis of Example 108k

Sources & evidence

ORD record
ord-41ad9b213e474fdfba4e668b83c6e7b8
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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