Acetyl chloride → HCID 59993355, compound

HRID 238211Notes

Reaction equation

HRID 238211 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]([N:14]1[CH2:19][CH2:18][N:17]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:16][CH2:15]1)[CH3:13])[N:6]([CH3:31])[C:5]2=[O:32].[C:33](Cl)(=[O:35])[CH3:34]>CN(C=O)C>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([N:17]2[CH2:16][CH2:15][N:14]([CH:12]([C:7]3[N:6]([CH3:31])[C:5](=[O:32])[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:33](=[O:35])[CH3:34])[CH:3]=4)[N:8]=3)[CH3:13])[CH2:19][CH2:18]2)(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 59993166HCID 59993166, compound

Product 1

HCID 59993355HCID 59993355, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the 1 ml DMF solution of 6-Amino-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-3H-quinazolin-4-one (50.0 mg, 0.11 mmol) was added acetyl chloride (9.44 mg, 0.12 mmol). The reaction was stirred for 2 hours. The solvent was removed by reduce pressure and extracted with Na2CO3 aqueous and ethyl acetate, dried over anhydrous MgSO4, and concentrated by rotary evaporation. Purification was accomplished by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase). The product was collected and dried under reduced pressure to give the N-(2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-4-oxo-3,4-dihydro-quinazolin-6-yl)-acetamide (Yield 8.29 mg, 14.9%). 1H NMR (400 MHz, MeOD-d4): δ 1.70 (d, 3H, J=6.57 Hz), 2.18 (s, 3H), 3.57-3.43 (m, 8H), 3.64 (s, 3H), 3.93 (s, 3H), 4.84 (q, 1H, J=6.57, 6.06 Hz), 7.19 (d, 2H, J=9.09 Hz), 7.64 (d, 1H, J=8.34 Hz), 7.79 (d, 2H, J=9.09 Hz), 7.98 (dd, 1H, J=8.59, 2.78 Hz), 8.46 (d, J=2.27 Hz). MS m/z calc. 499.2 found (ESI); 500.2 (M+1)+. Retention time 2.42 minutes.

Workup

  1. customThe solvent was removed
  2. extractionextracted with Na2CO3 aqueous and ethyl acetate
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customPurification
  6. customThe product was collected
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-844d02875b4043ad806fd34133778188
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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