Sodium Carbonate → HCID 24795031, compound

HRID 1096051Notes

Reaction equation

O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][S:12]([C:15]3[S:19][C:18]4[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:17]=4[C:16]=3[CH3:25])(=[O:14])=[O:13])[CH:9]=2)[CH2:4][CH2:3]1.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[BH4-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([NH:11][S:12]([C:15]4[S:19][C:18]5[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:17]=5[C:16]=4[CH3:25])(=[O:14])=[O:13])[CH:9]=3)[CH2:4][CH2:3]2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of N-(3-oxo-2,3-dihydro-1H-inden-5-yl)-5-chloro-3-methylbenzo[b]thiophene-2-sulfonamide (100 mg, 0.26 mmol), 1-methylpiperazine (0.28 ml, 2.6 mmol) and titanium (IV) isopropoxide (0.1 ml, 0.33 mmol) was heated at 50° C. for 30 min. The material was dissolved in ethanol and sodium borohydride (11 mg, 0.29 mmol) was added. After stirring at reflux for 3 hours, 2N sodium carbonate was added. The mixture was filtered and the filtrate was concentrated in vacuo. The resulting crude was purified by chromatography on silica gel, using as an eluent mixtures of methylene chloride/methanol/ammonia yielding 80 mg (65%) of N-[3-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-5-yl]-5-chloro-3-methylbenzo[b]thiophene-2-sulfonamide as a solid.

Workup

temperatureat reflux for 3 hours
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customThe resulting crude was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-ae32a9e9ab42448b9e0ddbc26c7902a8
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138210B2

Reaction notes

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