Acetyl chloride → HCID 10697412, compound

HRID 1003219Notes

Reaction equation

HRID 1003219 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[N:12]=[C:11]2[S:13][C:14]3[CH2:15][NH:16][CH2:17][CH2:18][C:19]=3[C:10]2=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:8]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:4][CH3:5])[CH3:2].[C:35](Cl)(=[O:37])[CH3:36].C(N(CC)CC)C.O1CCCC1>O>[C:35]([N:16]1[CH2:17][CH2:18][C:19]2[C:10]3[C:11]([S:13][C:14]=2[CH2:15]1)=[N:12][C:7]([CH2:6][N:3]([CH2:1][CH3:2])[CH2:4][CH3:5])=[C:8]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:9]=3[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10505011HCID 10505011, compound

Product 1

HCID 10697412HCID 10697412, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound obtained in Example 5A (2.00 g), acetyl chloride (0.19 g), triethylamine (0.37 ml) and tetrahydrofuran (10 ml) was stirred under ice cooling conditions for 3 hours. The reaction mixture was poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with chloroform-methanol (100:1, v/v) to yield ethyl 7-acetyl-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below) (0.65 g, 60%) as an amorphous solid having a melting point of 72 to 75° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. washeluted with chloroform-methanol (100:1

Sources & evidence

ORD record
ord-37e8ac583d1443bead61be8d4e9866d5
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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