HCID 59164483, compound → N-[6-(2-Hydroxy-2H-pyrazol-3-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

HRID 1441605Notes

Reaction equation

HRID 1441605 reaction equation
C([O:8][N:9]1[C:13]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][C:23]=2[C:24]([F:27])([F:26])[F:25])[NH:20][C:19](=[O:28])[N:18]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:17]3=[O:34])=[CH:12][CH:11]=[N:10]1)C1C=CC=CC=1>CO.[Pd]>[OH:8][N:9]1[C:13]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][C:23]=2[C:24]([F:27])([F:25])[F:26])[NH:20][C:19](=[O:28])[N:18]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:17]3=[O:34])=[CH:12][CH:11]=[N:10]1

Participants

4

Reactant 1

HCID 59164483HCID 59164483, compound

Product 1

HCID 45381813N-[6-(2-Hydroxy-2H-pyrazol-3-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamideYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-[6-(2-Benzyloxy-2H-pyrazol-3-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (100 mg, 0.202 mmol) was hydrogenated over 10% Pd/C in MeOH (5 mL) for 16 h at r.t. The catalyst was removed by filtration over Celite. The solution was concentrated in vacuo and the resulting resin was dissolved in DCM (1 mL). Hexanes (4 mL) was added and the precipitate was filtered off, washed with hexanes and dried to afford the title compound as a grey powder (66 mg, 81% yield). ES-MS: m/z 447.3 [M+CH3CN+H]+, rt 4.90 min. 1H-NMR (DMSO-d6, 400 MHz) 8.00 (s, H), 7.63 (s, 1H), 7.26 (d, J=2.34 Hz, 1H), 6.30 (d, J=1.89 Hz, 1H), 3.17 (s, 3H).

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionthe resulting resin was dissolved in DCM (1 mL)
  4. additionHexanes (4 mL) was added
  5. filtrationthe precipitate was filtered off
  6. washwashed with hexanes
  7. customdried

Sources & evidence

ORD record
ord-0c8f0c42de5546218977acc4458d9a52
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

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