Sodium Bicarbonate → HCID 135833322, compound

HRID 1003231Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[C:15]([S:40][C:10]=2[CH2:9]1)=[N:16][C:17]([CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39])=[C:18]([Cl:32])[C:19]=3[C:20]1[CH:25]=[CH:24][C:23]([O:26]C(C)C)=[C:22]([O:30][CH3:31])[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[C:15]([S:40][C:10]=2[CH2:9]1)=[N:16][C:17]([CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39])=[C:18]([Cl:32])[C:19]=3[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:30][CH3:31])[CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of titanium tetrachloride (6.3 g) in dichloromethane (10 ml) was added dropwise to a solution of the compound (3.8 g) obtained in Example 23B in dichloromethane (75 ml) under ice-cooling, and the mixture was stirred at 0° C. for 1.5 hours. The reaction mixture was poured over ice-aqueous saturated solution of sodium bicarbonate and the insoluble was filtered off, the organic layer was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (7:3, v/v) to yield 7-benzyl-3-chloro-4-(4-hydroxy-3-methoxyphenyl)-2-(2-oxo-1-pyrrolidinylmethyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine (0.89 g, 25%), which was then recrystallized as colorless prismatic crystals having a melting point of 190 to 191° C.

Workup

temperaturecooling
filtrationthe insoluble was filtered off
washthe organic layer was washed with water
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
washeluted with ethyl acetate-hexane (7:3

Sources & evidence

ORD record: ord-a8047cb6ad494ca987c70ff333949827
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046189

Reaction notes

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