Hydrochloric Acid → HCID 59164422, compound

HRID 1894022Notes

Reaction equation

HRID 1894022 reaction equation
CO[C:3](=[O:19])[C:4]1[CH:9]=[C:8]([C:10](=[O:13])[CH2:11][CH3:12])[C:7]([C:14]([F:17])([F:16])[F:15])=[CH:6][C:5]=1C.CC[N:22]([CH2:25]C)CC.[CH3:27][S:28]([NH:31][NH2:32])(=[O:30])=[O:29].[OH-:33].[Na+].Cl>C1COCC1.CCOC(C)=O>[O:33]=[C:25]1[N:32]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])[C:3](=[O:19])[C:4]2[C:5](=[CH:6][C:7]([C:14]([F:15])([F:16])[F:17])=[C:8]([C:10](=[O:13])[CH2:11][CH3:12])[CH:9]=2)[NH:22]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 269268MethanesulfonohydrazideHCID 67390427HCID 67390427, compound

Product 1

HCID 59164422HCID 59164422, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methyl-5-propionyl-4-trifluoromethyl-benzoic acid methyl ester (180 mg, 0.65 mmol) in THF (2.6 mL) was treated with (CCl3O)2CO (65.3 mg, 0.22 mmol) at r.t. under argon. The mixture was stirred for 15 min and Et3N (91 μL, 0.65 mmol) was added. The suspension was stirred for another 3 h and CH3SO2NHNH2 (73.5 mg, 0.65 mmol) was added. After 20 h, an aqueous solution of sodium hydroxide (1N, 0.87 mL) was added and the yellow suspension was stirred for 4 h at r.t. The pH of the mixture was then adjusted to 4-5 with an aqueous solution of hydrochloric acid (1N), and it was then diluted with EtOAc. The layers were separated and the organic phase was washed once with water, once with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was recrystallized in DCM to give N-(2,4-dioxo-6-propionyl-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (195 mg, 0.51 mmol, 79%) as a white solid, m.p. 234-236° C., ESI-MS: m/z 380 [M+H]+.

Workup

  1. stirringThe suspension was stirred for another 3 h
  2. waitAfter 20 h
  3. stirringthe yellow suspension was stirred for 4 h at r.t
  4. customThe layers were separated
  5. washthe organic phase was washed once with water, once with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was recrystallized in DCM

Sources & evidence

ORD record
ord-8a7f727d9fcf48eb81096a2c26a75a86
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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