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 971146노트

반응식

HRID 971146 반응식
[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]

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-291478feadc64061853b65b7ddbad6fc
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312214B2

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