Triethylamine → HCID 59242070, compound

HRID 1876155Notes

Reaction equation

HRID 1876155 reaction equation
[CH3:1][N:2]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([CH3:20])[N:11]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CCN(CC)CC.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:1][N:2]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([CH3:20])[N:11]=1)[C:3]1[CH:4]=[CH:5][C:6]([NH:9][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11311597N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine

Product 1

HCID 59242070HCID 59242070, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine 0.132 g (0.5 mmol) with Et3N 0.2 mL in CH2Cl2 10 mL was added methylsulfonyl chloride 0.115 g (1.0 mmol) at 23° C. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with CH2Cl2 30 mL, washed with water, sat. Na2CO3 aqueous solution and dried on anhydrous MgSO4. After removal of solvents, the crude product was subjected to gradient column chromatography (EtOAc/hexanes, 0% to 100%), but the compound was only obtained in <80% purity. Therefore, the crude compound was purified with preparative HPLC to give the titled compound in 15% yield. 1H NMR (CD3OD, 400 MHz): δ 7.86-7.82 (m, 1H), 7.72-7.67 (m, 1H), 7.44-7.42 (m, 4H), 7.29-7.24 (m, 1H), 6.94 (d, 1H, J=8.6 Hz), 3.84 (s, 3H), 3.07 (s, 3H), 2.78 (s, 3H). m/e: 343.1339 (M+1).

Workup

  1. washwashed with water, sat. Na2CO3 aqueous solution
  2. dry with materialdried on anhydrous MgSO4
  3. customAfter removal of solvents
  4. customthe compound was only obtained in <80% purity
  5. customTherefore, the crude compound was purified with preparative HPLC

Sources & evidence

ORD record
ord-c6596360567f46e2a2fb2eaa5e22a5e9
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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