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 906580Notes

Reaction equation

HRID 906580 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-ab5b97a214f5405c9a7a5be870b074d9
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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