HCID 59164499, compound → HCID 59164410, compound

HRID 906566Notes

Reaction equation

HRID 906566 reaction equation
C([N:4]([S:26]([CH3:29])(=[O:28])=[O:27])[N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([C:21]([F:24])([F:23])[F:22])=[C:11]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:12]=2)[NH:7][C:6]1=[O:25])(=O)C>Cl>[CH3:29][S:26]([NH:4][N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([C:21]([F:22])([F:24])[F:23])=[C:11]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:12]=2)[NH:7][C:6]1=[O:25])(=[O:28])=[O:27]

Participants

3

Reactant 1

HCID 59164499HCID 59164499, compound

Product 1

HCID 59164410HCID 59164410, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-[3-(acetyl-methanesulfonyl-amino)-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-ylmethyl]-acetamide (305 mg, 0.70 mmol) in 2M aq HCl (5 mL) was stirred at 80° C. for 1 d. Subsequently, the solvent was evaporated and the crude product was purified by preparative thin-layer chromatography (DCM/MeOH 8/2) to yield N-(3-methanesulfonylamino-2,4-dioxo-7-trifluoromethyl-1,2,3,4-tetrahydro-quinazolin-6-ylmethyl)-acetamide (22 mg, 0.056 mmol, 8%) as a light beige solid. 1H-NMR (DMSO-d6, 400 MHz) 3.13 ppm (s, 3H, SO2—CH3); LC-MS rt=2.35 min; MS: m/z 394.9 [M+H]+ Column: SunFireC18, 4.6*50 mn, 3.5 um; Positive MS Water/Acetonitrile 95:5 to 5:95 in 5 min, Flow: 1.5 mL/min

Workup

  1. customSubsequently, the solvent was evaporated
  2. customthe crude product was purified by preparative thin-layer chromatography (DCM/MeOH 8/2)

Sources & evidence

ORD record
ord-98e4891b86674599bf668da233e64c6e
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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