Hydrochloric Acid → HCID 67388416, compound

HRID 908489Notes

Reaction equation

HRID 908489 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH:13]=2)=[CH:5][C:4]=1[C:27]1[O:28][C:29]2[C:35]([CH2:36][OH:37])=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1>CC(O)C>[NH2:2][C:3]1[C:4]([C:27]2[O:28][C:29]3[C:35]([CH2:36][OH:37])=[CH:34][CH:33]=[CH:32][C:30]=3[N:31]=2)=[CH:5][C:6]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:13]=2)=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67388808HCID 67388808, compound

Product 1

HCID 67388416HCID 67388416, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
78 °C

Procedure

7N Hydrogen chloride in propanol-2 (1083 μl) was added to tert-butyl 4-[4-[6-amino-5-[7-(hydroxymethyl)-1,3-benzoxazol-2-yl]-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (93 mg). The mixture was heated at 78° C. for 1 hour. The solvent was evaporated under reduced pressure. A solution of 7N methanolic ammonia was added to the mixture at 0° C. The mixture was adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 2 to 10% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford [2-[2-amino-5-[1-(4-piperidyl)pyrazol-4-yl]-3-pyridyl]-1,3-benzoxazol-7-yl]methanol (46.0 mg) as a pale yellow solid. NMR Spectrum: (DMSOd6) 2.04-2.17 (m, 2H), 2.17-2.28 (m, 2H), 2.94-3.08 (m, 2H), 3.33-3.39 (m, 2H), 4.42-4.51 (m, 1H), 4.92 (d, 2H), 5.51 (t, 1H), 7.41 (dd, 1H), 7.46 (d, 1H), 7.65 (bs, 2H), 7.72 (d, 1H), 7.99 (s, 1H), 8.29 (s, 1H), 8.47 (d, 1H), 8.54 (d, 1H); Mass spectrum: M+H+ 391.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionA solution of 7N methanolic ammonia was added to the mixture at 0° C
  3. customThe crude product was purified by flash chromatography on silica gel eluting with 2 to 10% methanolic ammonia (7 N) in dichloromethane
  4. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-e97e8b9e011e4d8088464c4d3279ef18
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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