Methanol → HCID 68416902, compound

HRID 659123Notes

Reaction equation

HRID 659123 reaction equation
C[O:2][C:3](=[O:29])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH:13][C:14]([C:16]2[CH:17]=[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]=[CH:20][C:21]=2[F:22])=[O:15])[CH:7]=1.CO.[OH-].[Na+]>C1COCC1>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]=[CH:4][C:3]([OH:29])=[O:2])=[CH:7][C:8]=1[NH:13][C:14]([C:16]1[CH:17]=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:20][C:21]=1[F:22])=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68411982HCID 68411982, compound

Product 1

HCID 68416902HCID 68416902, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester (51) (124 mg, 0.21 mmol) was hydrolysed using Method C, except that MeOH (1.25 mL), THF and 1M NaOH (1.25 mL) were used, and the reaction was stirred for 3 hours. The solvent was removed under a stream of nitrogen gas and the residue acidified with 1N HCl. The solid was filtered and dried to give the title compound. Yield: 91 mg, 76%; LC-MS tr 2.28 min; HPLC Purity: 94%; MS (ES+) m/z 396 (M÷H); 1H NMR (400 MHz; DMSO): δ 6.60 (d, 1H), 7.45-7.75 (m, 7H), 7.80 (d, 2H), 7.95 (m, 1H), 8.10 (d, 1H), 8.15 (s, 1H), 10.25 (s, 1H), 12.55 (br. s, 1H)

Workup

  1. customThe solvent was removed under a stream of nitrogen gas
  2. filtrationThe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-1314b45c222e441c9f00b50b31941db3
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

Loading…