Hydrochloric Acid → HCID 11965454, compound

HRID 906525Notes

Reaction equation

HRID 906525 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[C:16]([F:19])([F:18])[F:17])[NH:12][C:11](=[O:20])[N:10]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:9]2=[O:26])(=[O:5])[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].O.Cl>C1COCC1.CO.CCOC(C)=O>[OH:5][CH:1]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[C:16]([F:18])([F:17])[F:19])[NH:12][C:11](=[O:20])[N:10]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:9]2=[O:26])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 53257565HCID 53257565, compound

Product 1

HCID 11965454HCID 11965454, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(6-butyryl-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (131 mg, 0.333 mmol) in THF (3 mL) and MeOH (3 mL) was added NaBH4 (131 mg, 3.32 mmol) portionwise over 10 min at r.t. The reaction mixture was stirred at r.t. for 18 h, poured onto a mixture of water and EtOAc then adjusted to pH 3-4 by addition of 1N aq HCl. The organic phase was washed twice with brine, dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (10 g silica gel, DCM/MeOH (1:0→9:1) to afford the title compound (94 mg, 71%) as colorless crystals. m.p.: 223-226° C., ESI-MS: m/z 396 [M+H]+, m/z 394 [M−H]−.

Workup

  1. washThe organic phase was washed twice with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography (10 g silica gel, DCM/MeOH (1:0→9:1)

Sources & evidence

ORD record
ord-5d637bd2987242709b3ba70bce9013b0
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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