Acetyl chloride → HCID 14500391, compound

HRID 1762825Notes

Reaction equation

HRID 1762825 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:21](=[O:22])[C:20]4[CH:23]=[CH:24][S:25][C:19]=4[NH:18][C:17]3=[O:26])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)CC)C>C(Cl)Cl>[C:29]([N:18]1[C:19]2[S:25][CH:24]=[CH:23][C:20]=2[C:21](=[O:22])[N:16]([CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:28][CH:27]=3)[CH2:9][CH2:10]2)[C:17]1=[O:26])(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14500390HCID 14500390, compound

Product 1

HCID 14500391HCID 14500391, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[2,3-d]pyrimidine-2,4-dione of Example 2 (1.7 g, 4.2 mmol), acetyl chloride (0.33 ml, 4.6 mmol) and triethylamine (1.8 ml, 12.6 mmol) in methylene chloride (40 ml) was stirred at room temperature for two days. The resultant solution was washed with H2O (2×50 ml), and then dried over magnesium sulfate. The solvent was evaporated in vacuo, and the resultant residue was purified by flash chromatography on silica gel 60 (80 g) using 2% methanol in methylene chloride as the eluant to give the named compound (1.3 g, 69% yield) as a colorless solid, mp 137°-141° C. IR(KBr): 1630, 1700 and 1775 cm-1 ; MS (DCI), m/z 444 (MH+); 1H NMR (CDCl3): δ 1.76-1.85 (m, 4H), 2.19-2.25 (m, 2H), 2.70 (t, J=7 Hz, 2H), 2.86 (s, 3H), 3.12-3.25 (m, 3H), 4.22 (t, J=7 Hz, 2H), 7.07 (d, J=6 Hz, 1H), 7.13 (t, J=8 Hz, 2H), 7.40 (d, J=6 Hz, 1H), 7.94-7.97 (m, 2H).

Workup

  1. washThe resultant solution was washed with H2O (2×50 ml)
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe resultant residue was purified by flash chromatography on silica gel 60 (80 g)

Sources & evidence

ORD record
ord-26eeae96c1174bdca1e8d9fedfe84508
Source dataset
uspto-grants-1989_05
Patent number
US04835157

Reaction notes

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