Water → HCID 135544626, compound

HRID 47857Notes

Reaction equation

HRID 47857 reaction equation
C([O:4][CH2:5][C:6]1[NH:15][C:14](=[O:16])[C:13]2[C:8](=[CH:9][C:10]([Cl:35])=[C:11]([CH2:17][N:18]([C:22]3[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:24][CH:23]=3)[CH2:19][C:20]#[CH:21])[CH:12]=2)[N:7]=1)(=O)C.[OH-].[Na+].O>C1COCC1>[Cl:35][C:10]1[CH:9]=[C:8]2[C:13]([C:14](=[O:16])[NH:15][C:6]([CH2:5][OH:4])=[N:7]2)=[CH:12][C:11]=1[CH2:17][N:18]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[CH:33][CH:34]=1)[CH2:19][C:20]#[CH:21]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 135509468HCID 135509468, compound

Product 1

HCID 135544626HCID 135544626, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (0.070 g, 0.14 mmol) in THF (2.7 ml) was dropwise added aqueous NaOH (1N, 0.27 ml, 0.27 mmol) followed by water (0.2 ml). The reaction mixture was stirred at room temperature for 2 hours, then the THF was removed in vacuo. The residue was suspended in water (10 ml) and the pH was adjusted to ˜5 with 1N HCl. The white precipitate was. collected by filtration, dried in vacuo and then it was reprecipitated from dichloromethane/hexanes to afford the title compound as a white solid (0.044 g, 70%), mp 185-187° C.; 1H-NMR (DMSO-d6) 1.49 (s, 9H, But), 3.25 (s, 1H, C≡CH), 4.35, 4.38 (2×s, 4H, CH2C≡C and 2-CH2), 4.78 (s, 2H, 6-CH2), 5.62 (br s, 1H, OH), 6.78 (d, J=8.7 Hz, 2H, 3′,5′-ArH), 7.73 (d, J=8.6 Hz, 2H, 2′,6′-ArH), 7.78, 7.84 (2×s, 2H, 5-H, 8-H), 12.07 (s, 1H, N3—H); FAB-HRMS: measured: 453.1463, calculated for C24H24ClN3O4: 453.1455.

Workup

  1. customthe THF was removed in vacuo
  2. filtrationcollected by filtration
  3. customdried in vacuo
  4. customit was reprecipitated from dichloromethane/hexanes

Sources & evidence

ORD record
ord-d8ef2d80518845ed9101246043457497
Source dataset
uspto-grants-2004_03
Patent number
US06699861B1

Reaction notes

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