Triethylamine → HCID 72311187, compound

HRID 1157471Notes

Reaction equation

HRID 1157471 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([NH:10][C:11](=[O:36])[CH2:12][N:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH:24]=[CH:25][CH2:26][CH2:27][OH:28])[CH:20]=2)[N:15]=[C:14]1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[C:6]([NH:10][C:11]([CH2:12][N:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH:24]=[CH:25][CH2:26][CH2:27][O:28][S:2]([CH3:1])(=[O:4])=[O:3])[CH:20]=2)[N:15]=[C:14]1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)=[O:36])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68524576HCID 68524576, compound

Product 1

HCID 72311187HCID 72311187, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (114 μL, 1.46 mmol) was added to a stirred solution of N-tert-butyl-2-[2-(3-chlorophenyl)-6-(4-hydroxybut-1-enyl)-4-oxo-4H-quinazolin-3-yl]acetamide (536 mg, 1.22 mmol) and triethylamine (510 μL, 3.66 mmol) in dry dichloromethane (12 mL) at 0° C. The cooling bath was removed after 2 h, and the mixture was stirred for an additional 3 h at room temperature. The reaction mixture was diluted with ethyl acetate (40 mL), and washed with 1 N HCl (aq.) (25 mL), sat. NaHCO3 (aq.) (25 mL) and brine (25 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford methanesulfonic acid 4-[3-(tert-butylcarbamoylmethyl)-2-(3-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-6-yl]but-3-enyl ester (528 mg, 1.02 mmol, 84%) as a yellow foam.

Workup

  1. customThe cooling bath was removed after 2 h
  2. additionThe reaction mixture was diluted with ethyl acetate (40 mL)
  3. washwashed with 1 N HCl (aq.) (25 mL), sat. NaHCO3 (aq.) (25 mL) and brine (25 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-852c28c1afbf454f8b7a0e153ea18fd0
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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