Hydrochloric Acid → 2-[(1-Methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride

HRID 2059945Notes

Reaction equation

HRID 2059945 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[ClH:35]>O1CCOCC1>[ClH:35].[CH3:12][CH:10]([O:9][C:8]1[CH:7]=[CH:6][C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][NH:22][CH2:23]4)[N:14]=2)=[CH:4][C:3]=1[C:1]#[N:2])[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 575059191,1-dimethylethyl 5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 685024052-[(1-Methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochlorideYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,1-dimethylethyl 5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 4; 53.7 mg, 0.117 mmol) and 4M HCl in dioxane (2 ml) was stirred at room temperature for 64 h. The mixture was concentrated in vacuo, the residue triturated with Et2O and dried in vacuo to leave a light brown solid (35.1 mg, 76%). 1H NMR (400 MHz, d6-DMSO) δ 9.52 (2H, br. s), 8.52 (1H, d), 8.40 (1H, dd), 8.02 (1H, dd), 7.57, (1H, d), 7.51-7.48 (2H, m), 4.99 (1H, sept.), 4.38 (2H, s), 3.39-3.34 (4H, m), 1.39 (6H, d); m/z (ES) 361 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated with Et2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-d26e2b91c4dc47bc918444e70f93eb68
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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