Hydrochloric Acid → HCID 11965379, compound

HRID 1894023Notes

Reaction equation

HRID 1894023 reaction equation
[O:1]=[C:2]1[N:11]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:10](=[O:17])[C:9]2[C:4](=[CH:5][C:6]([C:22]([F:25])([F:24])[F:23])=[C:7]([C:18](=[O:21])[CH2:19][CH3:20])[CH:8]=2)[NH:3]1.[BH4-].[Na+].Cl>C1COCC1.CO.CCOC(C)=O.O>[OH:21][CH:18]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[C:22]([F:24])([F:23])[F:25])[NH:3][C:2](=[O:1])[N:11]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:10]2=[O:17])[CH2:19][CH3:20]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59164422HCID 59164422, compound

Product 1

HCID 11965379HCID 11965379, compoundYield 78%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2,4-dioxo-6-propionyl-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (50 mg, 0.132 mmol) in THF (1 mL) and MeOH (1 mL) was added sodium borohydride (80 mg, 2.11 mmol). The resultant mixture was stirred for 20 h. After that time, it was then diluted with EtOAc and water and the pH was adjusted to 4-5 with an aqueous hydrochloric acid solution (1N). The organic phase was separated and washed once with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the crude product by flash chromatography (silica gel 60, DCM/MeOH 100:0→90:10) to afford N-[6-(1-hydroxy-propyl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (39 mg, 0.102 mmol, 78%) as a white powder, m.p. 219-222° C., 1H-NMR (DMSO-d6, 400 MHz) 11.93 (br s, 1H), 10.38 (br s, 1H), 8.33 (s, 1H), 7.50 (s, 1H), 5.63 (m, 1H), 5.27 (m, 1 H), 3.17 (s, 3H), 1.60 (m, 2H), 0.93 (m, 3H).

Workup

  1. customThe organic phase was separated
  2. washwashed once with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude product by flash chromatography (silica gel 60, DCM/MeOH 100:0→90:10)

Sources & evidence

ORD record
ord-b10a0cc58a05473e9cde76e282a82c6f
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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