Methanesulfonyl chloride → HCID 178493405, compound

HRID 336775Notes

Reaction equation

HRID 336775 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[NH:18][C:17](=[O:19])[C:16]3[C:11](=[CH:12][C:13]([O:22][CH3:23])=[CH:14][C:15]=3[O:20][CH3:21])[N:10]=2)=[CH:4][C:3]=1[CH3:24].[CH:25]([N:28]([CH:31](C)C)[CH2:29]C)(C)C.CS(Cl)(=O)=O>CN(C=O)C.CCOC(C)=O>[CH3:21][O:20][C:15]1[CH:14]=[C:13]([O:22][CH3:23])[CH:12]=[C:11]2[C:16]=1[C:17](=[O:19])[NH:18][C:9]([C:5]1[CH:6]=[C:7]([CH3:8])[C:2](/[N:1]=[CH:25]/[N:28]([CH3:31])[CH3:29])=[C:3]([CH3:24])[CH:4]=1)=[N:10]2

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 1360379832-(4-amino-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one

Product 1

HCID 178493405HCID 178493405, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-amino-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one (0.096 g, 0.295 mmol) and diisopropylethylamine (61.7 μL, 0.354 mmol), in DMF (2.96 mL) was added dropwise methanesulfonyl chloride (25.2 μL, 0.325 mmol). After stirring at room temperature for 18 h, the mixture was diluted with EtOAc (300 mL), washed with saturated aqueous sodium bicarbonate (2×75 mL), saturated aqueous LiCl (2×75 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified over silica gel (12 g, CH2Cl2/CH3OH) to provide (E)-N′-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenyl)-N,N-dimethylformimidamide (0.0502 g, 45%) as a white solid. Selected data: 1H NMR (300 MHz, DMSO-d6) δ 11.68 (s, 1H), 7.87 (s, 2H), 7.40 (s, 1H), 6.72 (d, J=2.31 Hz, 1H), 6.48 (d, J=2.31 Hz, 1H), 3.88 (s, 3H), 3.86 (s, 3H), 2.97 (s, 6H), 2.12 (s, 6H); MS (APCI) m/z 381 [M+H]+.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (2×75 mL), saturated aqueous LiCl (2×75 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified over silica gel (12 g, CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-7de4f9fd577d4cc8846d47a19de73bf9
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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