Hydrochloric Acid → 6-Methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)-3,4-dihydroquinazolin-4-one

HRID 855730Notes

Reaction equation

HRID 855730 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:19][CH2:18]1)[N:11]=[CH:10][N:9](COC(=O)C(C)(C)C)[C:8]2=[O:37].CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1.Cl>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:19][CH2:18]1)[N:11]=[CH:10][NH:9][C:8]2=[O:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 220308326-Methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 1357631226-Methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)-3,4-dihydroquinazolin-4-oneYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2M Aqueous sodium hydroxide (180 μl, 0.35 mmol) was added to a suspension of 6-methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (90 mg, 0.18 mmol) in methanol (3 ml). After stirring for 2 hours at ambient temperature, the mixture was adjusted to pH10 with 2M hydrochloric acid. The volatiles were removed under vacuum and the residue was suspended in water, filtered, washed with water followed by ether and dried under vacuum at 60° C. to give 6-methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)-3,4-dihydroquinazolin-4-one (55 mg, 79%).

Workup

  1. customThe volatiles were removed under vacuum
  2. filtrationfiltered
  3. washwashed with water
  4. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-76748cf69fd444a6b3570b705703f3d8
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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