Hydrochloric Acid → HCID 136004602, compound

HRID 547461Notes

Reaction equation

HRID 547461 reaction equation
CC1C=CC(C([O:8][CH:9]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[N:12]=[C:11]([CH:20]([N:26]([CH2:36][CH2:37][CH2:38][NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[NH:10]2)=O)=CC=1.O1CCCC1.[OH-].[Li+].Cl>O>[Cl:19][C:15]1[CH:14]=[C:13]2[C:18]([C:9](=[O:8])[NH:10][C:11]([CH:20]([N:26]([C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[CH2:36][CH2:37][CH2:38][NH:39][C:40](=[O:41])[O:42][C:43]([CH3:46])([CH3:44])[CH3:45])[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[N:12]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178425874HCID 178425874, compound

Product 1

HCID 136004602HCID 136004602, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-[1-[{3-[(tert-butoxycarbonyl)amino]propyl}(4-methylbenzoyl)amino]-2-(dimethylamino)-2-oxoethyl]-7-chloro-3,4-dihydroquinazolin-4-yl 4-methylbenzoate in a 1:1 mixture of tetrahydrofuran and water (20 ml), was added lithium hydroxide (284 mg, 2 eq.) at room temperature. The mixture was stirred at room temperature for 3 h. The reaction mixture was acidified with 1M of aqueous hydrogen chloride to pH 6-7 and later extracted into methylene chloride. The organic layer was washed with more water, dried over magnesium sulfate, filtered and concentrated. The product was purified by flash chromatography to give tert-butyl 3-[[1-(7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl](4-methylbenzoyl)amino]-propylcarbamate (257 mg) as a yellow solid.

Workup

  1. extractionlater extracted into methylene chloride
  2. washThe organic layer was washed with more water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-6a6c00c2af0b499c869f13783f510d96
Source dataset
uspto-grants-2011_05
Patent number
US07939539B2

Reaction notes

Loading…