p-Toluenesulfonic acid monohydrate → HCID 71765120, compound

HRID 2272978Notes

Reaction equation

HRID 2272978 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([OH:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=3)=[CH:6][N:5]2[CH:21]=1.[OH2:22].[C:23]1([CH3:33])C=CC(S(O)(=O)=O)=CC=1>C(O)CO>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:7]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([O:20][CH2:33][CH2:23][OH:22])([CH3:19])[CH3:18])=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:21]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 71765087HCID 71765087, compound

Product 1

HCID 71765120HCID 71765120, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a suspension of 28.6 mg (0.10 mmol) 7-fluoro-3-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-2H-pyrrolo[1,2-a]pyrazin-1-one in 0.45 ml ethane-1,2-diol is added 1.7 mg (0.01 mmol) toluene-4-sulfonic acid monohydrate. The reaction mixture is stirred for 5 days at ambient temperature. The reaction mixture is partitioned between water and ethylacetate. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 7-fluoro-3-{4-[1-(2-hydroxy-ethoxy)-1-methyl-ethyl]-phenyl}-2H-pyrrolo[1,2-a]pyrazin-1-one as white powder; HPLC/MS 2.17 min (B), [M+H] 331; 1H NMR (400 MHz, DMSO-d6) δ [ppm] 10.99 (s, 1H), 7.68-7.61 (m, 3H), 7.55-7.50 (m, 2H), 7.48 (dd, J=3.4, 1.9 Hz, 1H), 6.77 (d, J=1.9 Hz, 1H), 4.55 (t, J=5.6 Hz, 1H), 3.50 (q, J=5.5 Hz, 2H), 3.19 (t, J=5.6 Hz, 2H), 1.50 (s, 6H).

Workup

  1. customThe reaction mixture is partitioned between water and ethylacetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-c9384f160cee49c0a7753a61135cf027
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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