Potassium Carbonate → N-cyclopropyl-3-[6-(2-hydroxy-2-methyl-3-pyrrolidin-1-ylpropoxy)-4-oxoquinazolin-3(4H)-yl]-4-methylbenzamide

HRID 2354202Notes

Reaction equation

HRID 2354202 reaction equation
CC1C=CC(S(O[CH2:12][C:13]([OH:41])([CH3:40])[CH2:14][O:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]=[CH:21][N:20]([C:26]2[CH:31]=[C:30]([C:32]([NH:34][CH:35]4[CH2:37][CH2:36]4)=[O:33])[CH:29]=[CH:28][C:27]=2[CH3:38])[C:19]3=[O:39])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[NH:48]1[CH2:52][CH2:51][CH2:50][CH2:49]1>CN(C=O)C>[CH:35]1([NH:34][C:32](=[O:33])[C:30]2[CH:29]=[CH:28][C:27]([CH3:38])=[C:26]([N:20]3[C:19](=[O:39])[C:18]4[C:23](=[CH:24][CH:25]=[C:16]([O:15][CH2:14][C:13]([OH:41])([CH3:40])[CH2:12][N:48]5[CH2:52][CH2:51][CH2:50][CH2:49]5)[CH:17]=4)[N:22]=[CH:21]3)[CH:31]=2)[CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 86610962HCID 86610962, compound

Product 1

HCID 11282934N-cyclopropyl-3-[6-(2-hydroxy-2-methyl-3-pyrrolidin-1-ylpropoxy)-4-oxoquinazolin-3(4H)-yl]-4-methylbenzamideYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the crude 3-[(3-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-4-oxo-3,4-dihydroquinazolin-6-yl)oxy]-2-hydroxy-2-methylpropyl 4-methylbenzenesulfonate (0.2 g) in anhydrous DMF (10 ml) was added potassium carbonate (0.1 g) followed by pyrrolidine (0.15 g) and the mixture stirred at room temperature for 18 hours. The mixture was concentrated and purification by preparative HPLC provided the title compound as a gum (50 mg); NMR Spectrum: (CDCl3) 0.60 (m, 2H), 0.90 (m, 2H), 1.20 (m, 1H), 1.40 (s, 3H), 1.80 (m, 4H), 2.20 (s, 3H), 2.75 (m, 6H), 4.20 (m, 2H), 6.40 (s, 1H), 7.50 (m, 2H), 7.70 (m, 3F[), 7.80 (d, 1H), 7.90 (s, 1H); Mass Spectrum: M+H+ 477.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurification by preparative HPLC

Sources & evidence

ORD record
ord-2b96e871e402458ba14a29b9a18ef710
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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