Hydrochloric Acid → HCID 68469817, compound

HRID 1514260Notes

Reaction equation

HRID 1514260 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]([CH2:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])[CH2:25][CH2:24][CH2:23][C:22]=4[CH:37]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[ClH:38]>CCOCC>[ClH:38].[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]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:25][CH2:24][CH2:23][C:22]=4[CH:37]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:11])[CH3:12])#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59403456HCID 59403456, compound

Product 1

HCID 68469817HCID 68469817, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

1,1-Dimethylethyl 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl]propanoate (Preparation 12) (70 mg, 0.139 mmol) was treated with HCl (1045 μl, 4.18 mmol) (4N in dioxan) and warmed at 50° C. for 1.5 hours. A white precipitate started to form. Ether (0.5 ml) was added and the white solid filtered off and washed with ether to give the title compound (57 mg) on drying. δH (400 MHz, d6DMSO) 1.39 (6H, d), 1.91-1.96 (2H, m), 2.82 (2H, m), 3.12-3.21 (4H, m), 3.56 (2H, m), 4.62 (2H, s), 4.96-5.02 (1H, m), 7.57 (1H, d), 7.71 (1H, d), 7.99-8.01 (2H, m), 8.41 (1H, dd), 8.52 (1H, d), 10.3 (1H, v. broad s), 12.8 (1H, v. broad s); MS (ES) C25H26N4O4 requires 446; found 447.0 [M+H]+.

Workup

  1. customto form
  2. filtrationthe white solid filtered off
  3. washwashed with ether

Sources & evidence

ORD record
ord-2294b29badb940518540c480b3dbc511
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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