HCID 49779783, compound → HCID 49779842, compound

HRID 217623Notes

Reaction equation

HRID 217623 reaction equation
C(N(CC)[CH2:4][C:5]#[C:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]([C:24]4[C:25]([F:38])=[C:26]([NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:34])=[O:33])[CH:27]=[CH:28][C:29]=4[F:30])=[O:23])=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)=[CH:9][CH:8]=1)C>CO.[Pt](=O)=O>[F:38][C:25]1[C:24]([C:22]([C:21]2[C:15]3[C:16](=[N:17][CH:18]=[C:13]([C:10]4[CH:11]=[N:12][C:7]([CH2:6][CH2:5][CH3:4])=[CH:8][CH:9]=4)[CH:14]=3)[NH:19][CH:20]=2)=[O:23])=[C:29]([F:30])[CH:28]=[CH:27][C:26]=1[NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:34])=[O:33]

Participants

4

Reactant 1

HCID 49779783HCID 49779783, compound

Product 1

HCID 49779842HCID 49779842, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Propane-1-sulfonic acid (3-{5-[6-(3-diethylamino-prop-1-ynyl)-pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine-3-carbonyl}-2,4-difluoro-phenyl)-amide (P-2222, 20.3 mg, 0.0359 mmol) was dissolved in 0.14 mL of methanol. Platinum dioxide (0.81 mg, 0.0036 mmol) was added and the resulting mixture was stirred under an atmosphere of hydrogen for 1 hour. The mixture was filtered through a bed of celite and the filtrate was concentrated. The crude material was purified by flash silica gel chromatography, eluting with a gradient of 15% methanol in dichloromethane to 1% methanol in dichloromethane. The appropriate fractions were combined and concentrated to provide the desired compound as a solid. MS (ESI) [M+H+]+=499.4.

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude material was purified by flash silica gel chromatography
  4. washeluting with a gradient of 15% methanol in dichloromethane to 1% methanol in dichloromethane
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-18ee084870e7425c9334425c791b31ae
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

Loading…