Acetic Anhydride → 2-Acetylaminomethyl-7-benzyl-3-chloro-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine

HRID 1003229Notes

Reaction equation

HRID 1003229 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]2[S:9][C:10]3[CH2:11][N:12]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:13][CH2:14][C:15]=3[C:6]2=[C:5]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)[C:4]=1[Cl:33].[C:34](OC(=O)C)(=[O:36])[CH3:35]>N1C=CC=CC=1>[C:34]([NH:1][CH2:2][C:3]1[N:8]=[C:7]2[S:9][C:10]3[CH2:11][N:12]([CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:13][CH2:14][C:15]=3[C:6]2=[C:5]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)[C:4]=1[Cl:33])(=[O:36])[CH3:35]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 120436212-Aminomethyl-7-benzyl-3-chloro-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine

Product 1

HCID 120436182-Acetylaminomethyl-7-benzyl-3-chloro-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of the compound (0.3 g) obtained in Example 18B, acetic anhydride (0.142 g) and pyridine (2.5 ml) was stirred at room temperature for 1 hour and concentrated under reduced pressure. Ethyl acetate was added to the residue, which 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 to yield 2-acetylaminomethyl-7-benzyl-3-chloro-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine as an oil, which was then treated with ethanolic hydrochloride to yield the hydrochloride which was recrystallized from dichloromethane-ethyl ether to yield light-yellow powder having a melting point of 172 to 174° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate was added to the residue, which
  3. washwas washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-79611e02ab09421e8a4c9043aaa662dd
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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