Ammonia → HCID 54091288, compound

HRID 1433030Notes

Reaction equation

HRID 1433030 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)[C:14](=[O:27])[CH2:13]3)[NH:8][C:7]=2[CH:28]=1.[NH3:29]>CO>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:20]=[CH:21][C:22]([C:23]([NH2:29])=[NH:24])=[CH:25][CH:26]=4)[C:14](=[O:27])[CH2:13]3)[NH:8][C:7]=2[CH:28]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 54543987HCID 54543987, compound

Product 1

HCID 54091288HCID 54091288, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Hydrochloric acid is bubbled into an ice cooled solution of 4-[4-(6-chloro-1H-benzoimidazol-2-ylmethyl)-2-oxo-piperidin-1-ylmethyl]-benzonitrile (127 mg, 0.336 mmol) in 10 mL of methanol. The solution also contained 3Å molecular sieves. The reaction is stored at −30 for forty-eight hours. The methanol is condensed on the rotovap. Fresh methanol (15 mL) is added followed by a stream of ammonia gas. The reaction is heated to reflux for two and half hours. The reaction mixture is filtered at room temperature. Methanol is removed from the mother liquor. The resulting residue is purified by reverse phase HPLC (0-50% ACN/H2O). The product is isolated as a white solid with a melting point of 105-110° C. C21H22ClN5O MS m/z: 396,398. Anal. cald. for C21H22ClN5O.2C2HF3O2: C; 48.13; H, 3.88; N,11.22. Found: C, 45.05; H, 3.52; N, 9.89.

Workup

  1. waitThe reaction is stored at −30 for forty-eight hours
  2. customcondensed on the rotovap
  3. temperatureThe reaction is heated
  4. temperatureto reflux for two and half hours
  5. filtrationThe reaction mixture is filtered at room temperature
  6. customMethanol is removed from the mother liquor
  7. customThe resulting residue is purified by reverse phase HPLC (0-50% ACN/H2O)
  8. customThe product is isolated as a white solid with a melting point of 105-110° C

Sources & evidence

ORD record
ord-7abc0b8e17974d6299e3a24ef96fc5fd
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…