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 971146ノート

反応式

HRID 971146 の反応式
[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]

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-291478feadc64061853b65b7ddbad6fc
出典データセット
uspto-grants-2007_12
特許番号
US07312214B2

反応ノート

読み込み中…