Hydrochloric Acid → HCID 178422578, compound

HRID 1441572Notes

Reaction equation

HRID 1441572 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[C:25]([F:28])([F:27])[F:26])[NH:21][C:20](=[O:29])[N:19]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[C:18]3=[O:35])[N:5](CCOC[Si](C)(C)C)[N:6]=1.Cl.CCO>O1CCOCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[C:25]([F:27])([F:28])[F:26])[NH:21][C:20](=[O:29])[N:19]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[C:18]3=[O:35])[NH:5][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 59164460HCID 59164460, compound

Product 1

HCID 178422578HCID 178422578, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-{6-[5-methyl-2-(2-trimethylsilanylmethoxy-ethyl)-2H-pyrazol-3-yl]-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl}-methanesulfonamide (140 mg, 0.26 mmol) in dioxane (5 mL) was added a solution of HCl in EtOH (1N, 0.6 mL, 2 equiv). The solution was stirred at 60° C. for 4 h. The solvent was removed in vacuo and the resulting paste was sonicated in 5 mL of DCM. The solid was filtered off, washed with DCM and dried in vacuo to afford N-[6-(5-methyl-2H-pyrazol-3-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (59 mg, 56%) as a white solid. (ESI-MS: m/z 445.4 [M+CH3CN+H]+, rt 4.16 min)). 1H-NMR (DMSO-d6, 400 MHz) 12.0 (s, 1H), 10.36 (s, 1H), 8.13 (s, 1H), 7.62 (s, 1H), 6.22 (s, 1H), 3.15 (s, 3H), 2.28 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting paste was sonicated in 5 mL of DCM
  3. filtrationThe solid was filtered off
  4. washwashed with DCM
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c0031c7dc2ac4445b076452d0b54aa2e
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

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