Hydrochloric Acid → 6-{4-[1,1-dimethyl-2-(2-oxo-1-piperidinyl)ethyl]phenyl}-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide

HRID 971146Notes

Reaction equation

HRID 971146 reaction equation
[C:1]([C:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15]3[C:18]([C:29]([NH2:31])=[O:30])=[N:19][N:20]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[C:14]=3[C:13]2=[O:32])=[CH:8][CH:7]=1)([CH3:5])[CH3:4])#[N:2].Cl.Br[CH2:35][CH2:36][CH2:37][CH2:38][C:39](Cl)=[O:40].CC(C)([O-])C.[K+]>C(O)C.[Pd].C1COCC1>[CH3:4][C:3]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][C:15]3[C:18]([C:29]([NH2:31])=[O:30])=[N:19][N:20]([C:21]4[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=4)[C:14]=3[C:13]2=[O:32])=[CH:10][CH:11]=1)([CH3:5])[CH2:1][N:2]1[CH2:35][CH2:36][CH2:37][CH2:38][C:39]1=[O:40]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5211735-Bromovaleryl chlorideHCID 23665647Potassium tert-butoxideHCID 590200716-[4-(1-cyano-1-methylethyl)phenyl]-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide

Product 1

HCID 590196896-{4-[1,1-dimethyl-2-(2-oxo-1-piperidinyl)ethyl]phenyl}-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 6-[4-(1-cyano-1-methylethyl)phenyl]-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (0.17 g, 0.39 mmol) was hydrogenated at 40 psi in ethanol with 0.5 mL conc. HCl and 10% palladium on carbon (25 mg) for 72 h. The reaction was filtered and concentrated. To the amine in THF (5 mL) at 0° C. was added 5-bromovaleryl chloride (99 mg, 0.5 mmol) and TEA (1 mL) and the reaction was stirred 1 h. To the reaction was added potassium t-butoxide (0.24 g, 1.9 mmol) and the reaction was stirred 24 h. The reaction was quenched with water and extracted with ethyl acetate and dried (MgSO4). Purification by HPLC and freeze-drying afforded 15 mg (7.5%). Mass Spec (M+H)+ 516.3.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. stirringthe reaction was stirred 24 h
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. customPurification by HPLC
  8. customfreeze-drying
  9. customafforded 15 mg (7.5%)

Sources & evidence

ORD record
ord-291478feadc64061853b65b7ddbad6fc
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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