4-Methylbenzoyl Chloride → HCID 136038030, compound

HRID 336785Notes

Reaction equation

HRID 336785 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[NH:21][C:20](=[O:22])[C:19]3[C:14](=[CH:15][C:16]([O:25][CH3:26])=[CH:17][C:18]=3[O:23][CH3:24])[N:13]=2)=[CH:7][C:6]=1[CH3:27].[C:28]1([CH3:37])[CH:33]=[CH:32][C:31]([C:34](Cl)=[O:35])=[CH:30][CH:29]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:24][O:23][C:18]1[CH:17]=[C:16]([O:25][CH3:26])[CH:15]=[C:14]2[C:19]=1[C:20](=[O:22])[NH:21][C:12]([C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([O:4][CH2:3][CH2:2][NH:1][C:34](=[O:35])[C:31]3[CH:32]=[CH:33][C:28]([CH3:37])=[CH:29][CH:30]=3)=[C:6]([CH3:27])[CH:7]=1)=[N:13]2

Participants

5

Reactant 3

HCID 134054-Methylbenzoyl ChlorideHCID 81531DiisopropylethylamineHCID 136037976HCID 136037976, compound

Product 1

HCID 136038030HCID 136038030, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 2-(4-(2-aminoethoxy)-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one (0.060 g, 0.16 mmol), p-toluoyl chloride (0.028 mL, 0.21 mmol), and PS-DIEA (0.057 g, 0.21 mmol) in CH2Cl2 (4.0 mL) was stirred at room temperature for 16 h. The mixture was filtered, washed with CH2Cl2 and the solvent was removed under reduced pressure. The resulting residue was chromatographed on silica gel to yield N-(2-(4-(5,7-Dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy)ethyl)-4-methylbenzamide (0.037 g, 51%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 11.80-11.00 (s, 1H), 8.69 (t, J=5.43 Hz, 1H), 7.88 (s, 2H), 7.79 (d, J=8.19 Hz, 2H), 7.28 (d, J=8.00 Hz, 2H), 6.73 (d, J=2.31 Hz, 1H), 6.51 (d, J=2.31 Hz, 1H), 3.94 (t, J=5.59 Hz, 2H), 3.88 (s, 3H), 3.84 (s, 3H), 3.72-3.60 (m, 2H), 2.36 (s, 3H), 2.27 (s, 6H); MS (APCI) m/z 488 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with CH2Cl2
  3. customthe solvent was removed under reduced pressure
  4. customThe resulting residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-516b6689772a4f99a50fef3b4fe3725c
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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