Hydrochloric Acid → 1-[2-(3-{5-[3-Cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-4-piperidinecarboxylic acid

HRID 1942724Notes

Reaction equation

HRID 1942724 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([C:18]3[C:19]([CH2:37][CH3:38])=[C:20]([CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][CH:29]([C:32]([O:34]CC)=[O:33])[CH2:28][CH2:27]4)[CH:21]=[CH:22][CH:23]=3)=[N:15][N:14]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+].Cl>C(O)(C)C.O>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([C:18]3[C:19]([CH2:37][CH3:38])=[C:20]([CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][CH:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]4)[CH:21]=[CH:22][CH:23]=3)=[N:15][N:14]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][CH:10]([CH3:11])[CH3:12])#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66981810Ethyl 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-4-piperidinecarboxylate

Product 1

HCID 545793711-[2-(3-{5-[3-Cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-4-piperidinecarboxylic acidYield 24.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of ethyl 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-4-piperidinecarboxylate (D33) (64 mg) in isopropanol (3 mL) and water (3 mL) was added sodium hydroxide (50 mg). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was neutralized with 1 M HCl solution. The solvent was removed in vacuo. The residue was dissolved in THF, and filtered. The filtrate was purified by Mass Directed AutoPrep to give 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-4-piperidinecarboxylic acid (E11) (15 mg) as an off-white solid. δH (DMSO-d6, 400 MHz): 0.93 (6H, d), 1.12 (3H, t), 1.57 (2H, m), 1.79 (2H, m), 2.03 (3H, m), 2.20 (1H, m), 2.81 (8H, m), 3.25 (2H, m), 7.32 (1H, t), 7.44 (2H, d), 7.67 (1H, d), 8.31 (1H, dd), 8.45 (1H, s), 12.06 (1H, br s). MS (ES): C29H34N4O2S requires 502. found 503.2 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in THF
  3. filtrationfiltered
  4. customThe filtrate was purified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-f36e28659a4e499582403ed9eed15080
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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