Hydrochloric Acid → HCID 59275775, compound

HRID 555169Notes

Reaction equation

HRID 555169 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([C:20]2[CH:21]=[CH:22][C:23]3[O:27][C:26]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)=[C:25]([C:35](=[O:38])[NH:36][CH3:37])[C:24]=3[CH:39]=2)[C:18]=1[CH3:19])[C:12]([O:14]C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([C:20]2[CH:21]=[CH:22][C:23]3[O:27][C:26]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)=[C:25]([C:35](=[O:38])[NH:36][CH3:37])[C:24]=3[CH:39]=2)[C:18]=1[CH3:19])[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59275774HCID 59275774, compound

Product 1

HCID 59275775HCID 59275775, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of methyl 3-(benzyloxy)-5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoate (0.3 g, 0.57 mmol, 1 eq) in a 1:1 mixture of MeOH/THF at ambient temperature was added 5 eq. of NaOH, and the resulting mixture was heated to 60° C. for 5 h. The mixture was cooled to ambient temperature and then cooled in ice-water bath. The reaction mixture was acidified with 1.5 N HCl and then concentrated. The mixture with white precipitates was diluted with water and filtered to get the solid. It is further washed with water and dried in vacuum. Yield: 0.2 g (70%). 1H NMR (400 MHz, DMSO-d6): δ 2.19 (s, 3H), 2.82-2.83 (d, 3H, J=4.56 Hz), 5.27 (s, 2H), 7.34-7.46 (m, 6H), 7.50-7.55 (m, 4H), 7.60 (s, 1H), 7.75-7.77 (d, 1H, J=8.44 Hz), 7.99-8.03 (m, 2H), 8.49-8.50 (d, 1H), 13.0 (s, 1H). LCMS: (ES+) m/z=510 (M+H). Ascentis Express C18 (5.0×2.1-2.7 μm). Mphase A: 2% MeCN-98% H2O-10 mM NH4COOH. Mphase B: 98% MeCN-2% H2O-10 mM NH4COOH. Flow: 5 ml/Min.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. concentrationconcentrated
  3. customThe mixture with white precipitates
  4. additionwas diluted with water
  5. filtrationfiltered
  6. customto get the solid
  7. washIt is further washed with water
  8. customdried in vacuum

Sources & evidence

ORD record
ord-91c72e9105644f1a878411fbc94a2c94
Source dataset
uspto-grants-2011_11
Patent number
US08048887B2

Reaction notes

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