Acetyl chloride → HCID 66919080, compound

HRID 2354214Notes

Reaction equation

HRID 2354214 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]([C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:18]([NH:20][CH:21]1[CH2:23][CH2:22]1)=[O:19])[C:8]2=[O:28].[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[C:29]([NH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]([C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:18]([NH:20][CH:21]1[CH2:22][CH2:23]1)=[O:19])[C:8]2=[O:28])(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66918864HCID 66918864, compound

Product 1

HCID 66919080HCID 66919080, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[6-(2-Aminoethoxy)-4-oxoquinazolin-3(4H)-yl]-N-cyclopropyl-4-methylbenzamide (0.1 g), acetyl chloride (0.025 ml), and triethylamine (0.074 ml) were stirred in methylene chloride (2 ml) under an atmosphere of argon for 2 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (2×), brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting with 10% methanol/ethyl acetate gave the title compound (0.067 g) as a white solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 1.82 (s, 3H), 2.14 (s, 3H), 2.86 (m, 1H), 3.47 (m, 2H), 4.13 (m, 2H), 7.52 (m, 2H), 7.59 (s, 1H), 7.74 (d, 1H), 7.83 (s, 1H), 7.90 (d, 1H), 8.09 (t, 1H), 8.20 (s, 1H), 8.43 (d, 1); Mass Spectrum: M+H+ 421.

Workup

  1. washwashed with water (2×), brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated
  4. customPurification by column chromatography on a silica column
  5. washeluting with 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-6b5f7e283fc44c49b181b45046041f9e
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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