Hydrochloric Acid → HCID 44128663, compound

HRID 1514258Notes

Reaction equation

HRID 1514258 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][C:29]([O:31]C(C)(C)C)=[O:30])[CH2:25][CH2:24][CH2:23][C:22]=4[CH:36]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].Cl>>[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][C:29]([OH:31])=[O:30])[CH2:25][CH2:24][CH2:23][C:22]=4[CH:36]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 59403464HCID 59403464, compound

Product 1

HCID 44128663HCID 44128663, compound

Conditions

Temperature
50 °C

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-benzazepin-2-yl]acetate (Preparation 10) (85 mg, 0.174 mmol) was treated with HCl (1305 μl, 5.22 mmol) (4N soln in dioxan) and warmed at 50° C. for 2 hours. A white crystalline product formed. The reaction was cooled to RT and the solid filtered off and washed with ether. On drying the title compound was obtained (65 mg) as a white solid. δH (400 MHz, d6DMSO) 1.39 (6H, d), 1.91-2.00 (2H, m), 3.11-3.12 (2H, m), 3.59 (2H, m), 4.00 (2H, s), 4.60 (2H, s), 4.94-5.02 (1H, m), 7.53-7.59 (2H, m), 7.99-8.06 (2H, m), 8.41 (1H, dd), 8.52 (1H, d); MS (ES) C24H24N4O4 requires 432; found 433 [M+H]+.

Workup

  1. customA white crystalline product formed
  2. temperatureThe reaction was cooled to RT
  3. filtrationthe solid filtered off
  4. washwashed with ether
  5. dry with materialOn drying the title compound
  6. customwas obtained (65 mg) as a white solid

Sources & evidence

ORD record
ord-fdf32fe30d87471b8a577c8f6e347300
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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