Sodium Hydroxide → [6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]acetic acid

HRID 2059954Notes

Reaction equation

HRID 2059954 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:36])[CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:19]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH:31]([CH3:33])[CH3:32])=[C:26]([C:34]#[N:35])[CH:25]=4)[O:21][N:20]=3)[C:14]=2[CH3:18])[CH2:9]1)C>C(O)C>[C:34]([C:26]1[CH:25]=[C:24]([C:22]2[O:21][N:20]=[C:19]([C:13]3[C:14]([CH3:18])=[C:15]4[C:10](=[CH:11][CH:12]=3)[CH2:9][N:8]([CH2:7][C:6]([OH:36])=[O:5])[CH2:17][CH2:16]4)[N:23]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH:31]([CH3:33])[CH3:32])#[N:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57505854ethyl[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]acetate

Product 1

HCID 44125169[6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]acetic acidYield 9.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2M Sodium hydroxide (2 ml) was added to a suspension of ethyl[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]acetate (Preparation 23; 80 mg, 0.17 mmol) in ethanol (2 ml). The reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated and the residue diluted with water (5 ml). The solution was acidified with acetic acid and extracted with ethyl acetate (3×5 ml). The aqueous phase was evaporated and the residue purified by MDAP to give the title compound as a colourless solid (7 mg). 1H NMR (400 MHz, d4MeOH) δ: 1.46 (6H, d), 2.55 (3H, s), 3.19 (2H, t), 3.35 (2H, s), 3.67 (2H, t), 3.78 (2H, s), 4.53 (2H, s), 4.95 (1H, m) (part obscured by water peak), 7.20 (1H, d), 7.54 (1H, d), 7.85 (1H, d), 8.50-8.60 (2H, m).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with water (5 ml)
  3. extractionextracted with ethyl acetate (3×5 ml)
  4. customThe aqueous phase was evaporated
  5. customthe residue purified by MDAP

Sources & evidence

ORD record
ord-87f10a2ef4d5430aba8802b4a7831019
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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