Triethylamine → HCID 66918727, compound

HRID 2354220Notes

Reaction equation

HRID 2354220 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C@@H:26]5[CH2:30][CH2:29][CH2:28][NH:27]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.C([O:42][CH2:43][C:44](Cl)=[O:45])(=O)C.[OH-].[Na+]>C(Cl)Cl.CO>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C@@H:26]5[CH2:30][CH2:29][CH2:28][N:27]5[C:43](=[O:42])[CH2:44][OH:45])[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 26297Acetoxyacetyl chlorideHCID 66918942HCID 66918942, compound

Product 1

HCID 66918727HCID 66918727, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-Cyclopropyl-4-methyl-3-[4-oxo-6-[(2S)-pyrrolidin-2-ylmethoxy]quinazolin-3(4H)-yl]benzamide (0.20 g), triethylamine (0.133 ml), and acetoxyacetyl chloride (0.077 ml) were stirred in methylene chloride (2 ml) under argon at room temperature for 30 minutes. A solution of 2N NaOH (2 ml) and methanol (2 ml) was added to the reaction mixture and stirring continued for 1 hour at room temperature. The reaction mixture was diluted with methylene chloride and washed with brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting with 5% methanol/ethyl acetate to give the title compound (0.113 g) as a white foam solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.70 (m, 2H), 1.83-2.10 (m, 4H), 2.14 (s, 3H), 2.86 (m, 1H), 3.40 (m, 2H), 4.05 (m, 3H), 4.25 (m, 1H), 4.32 (m, 1H), 4.52 (t, 1H), 7.53 (m, 2H), 7.60 (s, 1H), 7.74 (d, 1H), 7.84 (s, 1H), 7.91 (d, 1M, 8.19 (s, 1H), 8.43 (d, 1H); Mass Spectrum: M+H+ 477.

Workup

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

Sources & evidence

ORD record
ord-2fb55ba6c04b48998aef38bfd4ba23a8
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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