Hydrochloric Acid → HCID 60152475, compound

HRID 537507Notes

Reaction equation

HRID 537507 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[N:5][N:6]([C:8]2[CH:34]=[CH:33][C:11]([O:12][CH:13]([C:17]3[CH:32]=[CH:31][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[O:22])=[CH:19][N:18]=3)[CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[CH:7]=1.[OH-].[Na+].Cl>CO>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:4]=[N:5][N:6]([C:8]2[CH:9]=[CH:10][C:11]([O:12][CH:13]([C:17]3[CH:32]=[CH:31][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[CH:19][N:18]=3)[CH2:14][CH2:15][CH3:16])=[CH:33][CH:34]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium Hydroxide2×HCID 68178603HCID 68178603, compound

Product 1

HCID 60152475HCID 60152475, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(+/−)-Ethyl 3-(6-(1-(4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)nicotinamido)propanoate (45 mg, 0.089 mmol) was dissolved in methanol (2 mL). 1 M NaOH (2 mL) was added with stirring at room temperature. After stirring for 6 hours, 1M HCl (2 mL) was added. The pH was adjusted to approximately 4, using 1M HCl and 1M NaOH. The resulting cloudy solution was extracted with ethyl acetate (2×15 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give (+/−)-3-(6-(1-(4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)nicotinamido)propanoic acid (42 mg, 100%) as a foamy solid. 1H NMR (400 MHz, CDCl3, δ): 9.23 (d, J=1.6 Hz, 1H), 8.38 (dd, J=8.2, 2.1 Hz, 1H), 7.99 (s, 1H), 7.85-7.80 (m, 2H), 7.55 (d, 1H), 7.49-7.42 (m, 2H), 6.92-6.85 (m, 2H), 5.31 (dd, J=7.7, 4.8 Hz, 1H), 3.83-3.76 (m, 2H), 2.75-2.69 (m, 2H), 2.09-1.85 (m, 2H), 1.60-1.39 (m, 2H), 0.96 (t, J=7.3 Hz, 3H). MS (M+1): 477.3.

Workup

  1. stirringAfter stirring for 6 hours
  2. extractionThe resulting cloudy solution was extracted with ethyl acetate (2×15 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1c3f02c62dfa4338a73c2f8003e99c73
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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