Hydrochloric Acid → HCID 68469902, compound

HRID 1514257Notes

Reaction equation

HRID 1514257 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24][CH2:23][C:22]=4[CH:35]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[ClH:36]>CCOCC>[ClH:36].[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:19]=[CH:20][C:21]4[CH2:27][NH:26][CH2:25][CH2:24][CH2:23][C:22]=4[CH:35]=3)[N:14]=2)=[CH:4][C:3]=1[C:1]#[N:2])[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59403458HCID 59403458, compound

Product 1

HCID 68469902HCID 68469902, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1,1-Dimethylethyl 7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carboxylate (Preparation 9) (310 mg, 0.653 mmol) was treated with HCl (3266 μl, 13.06 mmol) (4N in dioxan) and stirred. After 30 minutes a white precipitate had formed. After 1 hour ether (2 ml) was added and the precipitate filtered off and washed with ether. The title compound (230 mg) was obtained on drying. δH (400 MHz, d6DMSO) 1.39 (6H, d), 1.91 (2H, m), 3.11-3.13 (2H, m), 3.37-3.40 (2H, m), 4.42 (2H, s), 4.94-5.02 (1H, m), 7.57 (1H, d), 7.64 (1H, d), 7.96-8.00 (2H, m), 8.41 (1H, dd), 8.52 (1H, d), 9.04 (2H, broad s); MS (ES) C22H22N4O2 requires 374; found 375.0 [M+H]+.

Workup

  1. customAfter 30 minutes a white precipitate had formed
  2. filtrationthe precipitate filtered off
  3. washwashed with ether

Sources & evidence

ORD record
ord-ea61a845b42b4343b0f03fd8848b5826
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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