Hydrochloric Acid → 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanoic acid hydrochloride

HRID 2059948Notes

Reaction equation

HRID 2059948 reaction equation
C(O)=O.[C:4]([C:6]1[CH:7]=[C:8]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:30]=[CH:29][CH:28]=[C:27]4[C:22]=3[CH2:23][CH2:24][N:25]([CH2:31][CH2:32][C:33]([O:35]C)=[O:34])[CH2:26]4)[N:17]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])#[N:5].[Li+].[OH-].Cl.C(Cl)[Cl:41]>C1COCC1.CO.O>[ClH:41].[C:4]([C:6]1[CH:7]=[C:8]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:30]=[CH:29][CH:28]=[C:27]4[C:22]=3[CH2:23][CH2:24][N:25]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH2:26]4)[N:17]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 68498188Methyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanoate formic acid salt

Product 1

HCID 685018803-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanoic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of methyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanoate formic acid salt (Preparation 6, 5.9 mg, 0.0132 mmol) and LiOH (0.15 mg) in THF-MeOH-water (300 μl, 300 μl, 100 μl) was irradiated to 100° C. for 3 min in the microwave. 2M aqueous HCl (1 ml) and DCM (2 ml) were added sequentially, and a precipitate formed. Filtration gave the title compound as a white solid (6.5 mg, quant.). 1H NMR (400 MHz, d6-DMSO) δ 12.71 (1H, br s), 11.41 (1H, br s), 8.53 (1H, d), 8.41 (1H, dd), 8.05 (1H, d), 7.57 (1H, d), 7.53 (1H, t), 7.46 (1H, d), 4.99 (1H, sept), 4.53 (2H, br s), 3.46-3.43 (4H, m), 3.65 (2H, br s), 2.98 (2H, t), 1.39 (6H, d); m/z (ES) 433 [M+H+].

Workup

  1. customa precipitate formed
  2. filtrationFiltration

Sources & evidence

ORD record
ord-d6538684e3164bd4a023e475da80e2b9
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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