Triethylamine → HCID 66918809, compound

HRID 2354212Notes

Reaction equation

HRID 2354212 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].[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH:21]1([NH:20][C:18](=[O:19])[C:17]2[CH:24]=[CH:25][C:26]([CH3:27])=[C:15]([N:9]3[C:8](=[O:28])[C:7]4[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH2:3][CH2:2][NH:1][S:30]([CH3:29])(=[O:32])=[O:31])[CH:6]=4)[N:11]=[CH:10]3)[CH:16]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66918864HCID 66918864, compound

Product 1

HCID 66918809HCID 66918809, 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), methanesulfonyl chloride (0.027 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 (0.106 g) as a white solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.15 (s, 3H), 2.85 (m, 1H), 2.96 (s, 3H), 3.41 (m, 2H), 4.19 (t, 2H), 7.30 (t, 1H), 7.54 (m, 2H), 7.60 (s, 1H), 7.75 (d, 1H), 7.84 (s, 1H), 7.91 (d, 1H), 8.20 (s, 1H), 8.43 (d, 1H); Mass Spectrum: M+H+ 457.

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-f0af32450e81494aaec0578414d84de3
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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