Hydrochloric Acid → N-[3-(3-{2-[(2-Amino-2,3-dihydro-1H-inden-5-yl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide

HRID 1159981Notes

Reaction equation

HRID 1159981 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:33])[C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[CH3:34][C:35]1[N:36]=CO[C:39]=1[C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][CH:46]=1)[NH2:43].Cl>C(O)(C)C>[NH2:36][CH:35]1[CH2:39][C:40]2[C:46](=[CH:45][CH:44]=[C:42]([NH:43][C:2]3[N:7]=[C:6]([C:8]4[C:9]([C:17]5[CH:18]=[C:19]([NH:23][C:24](=[O:33])[C:25]6[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=6[F:32])[CH:20]=[CH:21][CH:22]=5)=[N:10][N:11]5[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=45)[CH:5]=[CH:4][N:3]=3)[CH:41]=2)[CH2:34]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 595114203-(4-Methyl-1,3-oxazol-5-yl)anilineHCID 59513803N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide

Product 1

HCID 59513754N-[3-(3-{2-[(2-Amino-2,3-dihydro-1H-inden-5-yl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by heating N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (180 mg, 0.39 mmol) (prepared according to a procedure similar to that described in Example 27, Step C), 3-(4-methyl-1,3-oxazol-5-yl)aniline (75 mg, 0.43 mmol), hydrochloric acid (40 μL, 0.040 mmol, 1M HCl/Et2O) and isopropanol (2 mL) at 160° C. for 15 min in a microwave synthesizer. The reaction was cooled and concentrated and purified by silica gel column chromatography (20-100% gradient EtOAc (0.5% TEA)/hexanes (0.5% TEA)). Purification yielded 60 mg (25%) of a yellow powder. ESIMS (M+H)+=601.17.

Workup

  1. customprepared
  2. customat 160° C.
  3. customfor 15 min
  4. temperatureThe reaction was cooled
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (20-100% gradient EtOAc (0.5% TEA)/hexanes (0.5% TEA))
  7. customPurification

Sources & evidence

ORD record
ord-82a713f4588042ad94a92e57be3648f5
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

Loading…