Sodium Hydroxide → GSK-2262167 sodium

HRID 2059955Notes

Reaction equation

HRID 2059955 reaction equation
[OH-].[Na+:2].[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[C:21]([CH3:37])=[C:22]4[C:27](=[CH:28][CH:29]=3)[CH2:26][N:25]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[CH2:24][CH2:23]4)[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4]>C(O)C.O>[Na+:2].[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[C:21]([CH3:37])=[C:22]4[C:27](=[CH:28][CH:29]=3)[CH2:26][N:25]([CH2:30][CH2:31][C:32]([O-:34])=[O:33])[CH2:24][CH2:23]4)[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57505851Ethyl 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate

Product 1

HCID 53249052GSK-2262167 sodium

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2M sodium hydroxide (2 ml) was added to a solution of ethyl 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate (Preparation 24; 80 mg, 0.17 mmol) in ethanol (2 ml) at 60° C. The reaction mixture was stirred at 60° C. for 2 hours, cooled to room temperature and diluted with water (2 ml). The solid was filtered off, washed with a small amount of water and dried to give the title compound as a colourless solid (55 mg). 1H NMR (400 MHz, d6DMSO) δ: 1.39 (6H, d), 2.08 (2H, t), 2.44 (3H, s), 2.59-2.78 (6H, m), 3.56 (2H, s), 4.98 (1H, m), 7.09 (1H, d), 7.55 (1H, d), 7.65 (1H, d), 8.40 (1H, dd), 8.50 (1H, s). MS m/z 447 [MH]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe solid was filtered off
  3. washwashed with a small amount of water
  4. customdried

Sources & evidence

ORD record
ord-8ab1c98732ad4a6488ed3af36e0b612f
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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