Hydrochloric Acid → HCID 11384142, compound

HRID 854864Notes

Reaction equation

HRID 854864 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[C:12]([C:21]([O:23]CC)=[O:22])[CH:13]([C:17]([F:20])([F:19])[F:18])[O:14]3)=[CH:9][C:8]=2[Cl:26])=[C:4]([F:29])[CH:3]=1.[OH-].[Na+].Cl>CO.C1COCC1>[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[C:12]([C:21]([OH:23])=[O:22])[CH:13]([C:17]([F:20])([F:18])[F:19])[O:14]3)=[CH:9][C:8]=2[Cl:26])=[C:4]([F:29])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69518704HCID 69518704, compound

Product 1

HCID 11384142HCID 11384142, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester from Step 2 (0.10 g, 0.23 mmole) was dissolved in 0.5 mL methanol and 0.5 mL THF. Sodium hydroxide (2.5 N) (0.2 mL, 0.46 mmole) was added to above solution and stirred at room temperature for overnight. The reaction mixture was acidified with 0.5 N HCl. The compound was extracted out with EtOAc. The organic layer was washed with water and dried over anhydrous MgSO4. The filtrate was evaporated and dried in vacuo to afford the title compound as a yellow solid (0.07 g, 75%): LCMS m/z 402.85 (M+H). 1H NMR (acetone-d6/400 MHz) 7.89 (s, 1H), 7.73 (s, 1H), 7.67 (dd, 1H, J=10.8, 2.4 Hz), 7.53 (dd, 1H, J=10, 1.6 Hz), 7.47 (m, 1H), 5.81 (q, 1H, J=7.0 Hz).

Workup

  1. extractionThe compound was extracted out with EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. customThe filtrate was evaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-76285f867b7f466db5877df414f4df40
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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