Water → HCID 136236977, compound

HRID 1050957Notes

Reaction equation

HRID 1050957 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[NH:6][C:5]2=[O:22].[OH2:23].[C:24]1([CH3:34])C=CC(S(O)(=O)=O)=CC=1.O>C(O)CO>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:13]=[CH:14][C:15]([C:18]([O:21][CH2:34][CH2:24][OH:23])([CH3:20])[CH3:19])=[CH:16][CH:17]=1)[NH:6][C:5]2=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 136236970HCID 136236970, compound

Product 1

HCID 136236977HCID 136236977, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a suspension of 6-fluoro-2-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-3H-quinazolin-4-one (149 mg, 0.50 mmol) in ethane-1,2-diol (2 ml) is added toluene-4-sulfonic acid monohydrate (114 mg, 0.60 mmol). The reaction mixture is stirred for 3 hours at ambient temperature. The suspension is then heated to 80° C. and the resulting clear solution is stirred at this temperature for 5 hours. The reaction mixture is cooled to room temperature and water is added. The resulting precipitate is filtered off and washed with water. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 6-fluoro-2-{4-[1-(2-hydroxy-ethoxy)-1-methyl-ethyl]-phenyl}-3H-quinazolin-4-one as white crystals; HPLC/MS 2.28 min (B), [M+H] 343;

Workup

  1. temperatureThe suspension is then heated to 80° C.
  2. stirringthe resulting clear solution is stirred at this temperature for 5 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed with water
  6. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-25bbca88d79a48d19de5f076e0ecedf8
Source dataset
uspto-grants-2016_07
Patent number
US09388142B2

Reaction notes

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