Tetrahydrofuran → HCID 68156800, compound

HRID 1892805Notes

Reaction equation

HRID 1892805 reaction equation
[CH3:1][C:2]([CH3:36])([CH3:35])[CH:3]([C:20]1[CH:34]=[CH:33][C:23]([C:24]([NH:26][CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[O:25])=[CH:22][CH:21]=1)[NH:4][C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[N:12]2)=[CH:9][CH:10]=1.C1COCC1.[OH-].[Na+]>CO>[CH3:1][C:2]([CH3:36])([CH3:35])[CH:3]([C:20]1[CH:34]=[CH:33][C:23]([C:24]([NH:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:25])=[CH:22][CH:21]=1)[NH:4][C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=[N:12]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86669099HCID 86669099, compound

Product 1

HCID 68156800HCID 68156800, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 20 drams vial was charged with methyl (±)-3-(4-(2,2-dimethyl-1-((6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)amino)propyl)benzamido)propanoate (92 mg, 0.18 mmol), THF (1.8 mL) and MeOH (1.8 mL). NaOH 1M aq. (0.9 mL) was then added in one portion and the resulting mixture stirred for 30 minutes at room temperature. Organic solvents removed under reduced pressure and 5 mL of water added to the vial. Under magnetic stirring, citric acid solution (10%, aq.) added dropwise to reach ca. pH 3. The solid formed was recovered with a büchner funnel, washed with water and dried under high vacuum to provide (±)-3-(4-(2,2-dimethyl-1-((6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)amino)propyl)benzamido)propanoic acid as a white solid (76.9 mg, 86.0%). 1H NMR (400 MHz, DMSO-d6) δ 0.98 (s, 9H) 2.44-2.48 (m, 2H) 3.38-3.47 (m, 2H) 4.33 (d, J=8.22 Hz, 1H) 6.54 (d, J=8.41 Hz, 1H) 7.17 (dd, J=8.90, 2.84 Hz, 1H) 7.44 (d, J=8.22 Hz, 2H) 7.55 (d, J=9.00 Hz, 1H) 7.74 (d, J=8.41 Hz, 2H) 7.84 (d, J=2.54 Hz, 1H) 8.08 (s, 1H) 8.44 (t, J=5.28 Hz, 1H) 8.84 (s, 1H) 12.18 (br. s., 1H); MS (M+1): 490.4.

Workup

  1. customOrganic solvents removed under reduced pressure and 5 mL of water
  2. additionadded to the vial
  3. additionUnder magnetic stirring, citric acid solution (10%, aq.) added dropwise
  4. customThe solid formed
  5. customwas recovered with a büchner funnel
  6. washwashed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-aad321d6513e477d8d42870a9aa7d452
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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