HCID 66664639, compound → HCID 66665016, compound

HRID 1773605Notes

Reaction equation

HRID 1773605 reaction equation
[C:1]([O:5][C:6](=[O:45])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][CH:21]=[N:22]3)=[CH:17][C:16]=2[NH:25][C:26]([C:28]2[CH:29]=[N:30][N:31]3[CH:36]=[C:35]([O:37]CC4C=CC=CC=4)[CH:34]=[N:33][C:32]=23)=[O:27])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:45])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][CH:21]=[N:22]3)=[CH:17][C:16]=2[NH:25][C:26]([C:28]2[CH:29]=[N:30][N:31]3[CH:36]=[C:35]([OH:37])[CH:34]=[N:33][C:32]=23)=[O:27])[CH2:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66664639HCID 66664639, compound

Product 1

HCID 66665016HCID 66665016, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1-{6-[(6-benzyloxy-pyrazolo[1,5-a]pyrimidine-3-carbonyl)-amino]-quinolin-7-yl}-piperidin-4-ylmethyl)-carbamic acid tert-butyl ester (0.4 g) and palladium on carbon (10%, 50 mg) in ethanol (20 mL) was stirred under hydrogen atmosphere (balloon pressure) for 2 days. The resulting mixture was filtered over a CELITE™ pad and the filtrate was evaporated under reduced pressure. The crude residue was purified by flash chromatography to afford 0.220 g of (1-{6-[(6-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carbonyl)-amino]-quinolin-7-yl}-piperidin-4-ylmethyl)-carbamic acid tert-butyl ester as a yellow solid.

Workup

  1. filtrationThe resulting mixture was filtered over a CELITE™ pad
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0093e0e68ada4535a0d676128de4c93b
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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