Hydrochloric Acid → 2-(Methyloxy)-5-[3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride

HRID 1514279Notes

Reaction equation

HRID 1514279 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:33]=[CH:32][C:19]4[CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][CH2:24][C:18]=4[CH:17]=3)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])#[N:2].O1CCOCC1.[ClH:40]>>[ClH:40].[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:33]=[CH:32][C:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:18]=4[CH:17]=3)[N:12]=2)=[CH:4][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 684667951,1-Dimethylethyl 7-{5-[3-cyano-4-(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 684689682-(Methyloxy)-5-[3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochlorideYield 62.7%

Procedure

A solution of 1,1-dimethylethyl 7-{5-[3-cyano-4-(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 54) (280 mg, 0.627 mmol) in hydrochloric acid 4M solution in dioxane (5 ml, 20.00 mmol) and 1,4-dioxane (5 ml) was stirred at room temperature overnight. The reaction mixture was filtered and washed with dioxane (˜5 ml), and the solid dried under vacuum to yield the title compound (177 mg, 0.393 mmol, 62.7% yield) as an off white solid. δH (d6DMSO, 400 MHz): 8.99-9.31 (2H, m), 8.53 (1H, s), 8.46 (1H, d), 7.96 (1H, s), 7.93 (1H, d), 7.54 (1H, d), 7.46 (1H, d), 4.07 (3H, s), 3.09-3.31 (7H, m); MS (ES): C20H18N4O2 requires 346; found 347 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with dioxane (˜5 ml)
  3. customthe solid dried under vacuum

Sources & evidence

ORD record
ord-79194a44cf604783a7438d6606fa4405
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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