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 1172511Notes

Reaction equation

HRID 1172511 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-81fe8c65d7dd4e7d93920180ecfbc926
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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