HCID 66880892, compound → 2-(4-(3-Amino-6-methyl-quinolin-4-ylamino)phenyl)-2-methylpropanenitrile

HRID 476159Notes

Reaction equation

HRID 476159 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[C:23]#[N:24])=[CH:18][CH:17]=1.[H][H]>C1COCC1.CO.[Pd]>[NH2:12][C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:26])[C:23]#[N:24])=[CH:18][CH:17]=1)=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 66880892HCID 66880892, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 668804232-(4-(3-Amino-6-methyl-quinolin-4-ylamino)phenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-(4-(6-Methyl-3-nitroquinolin-4-ylamino)phenyl)-2-methylpropanenitrile (Compound of Preparation 1,600 mg, 1.73 mmol) and 10% Pd—C (90 mg) were shaken in 15 mL of THF-MeOH (1:1) under 25 psi of hydrogen for 3 hours at RT. After completion of reaction, the catalyst was filtered-off and the filtrate was evaporated to dryness to obtain the title compound. Yield: 250 mg (46%); 1H NMR (DMSO-d6, 300 MHz): δ 8.507 (s, 1H), 7.819 (s, 1H), 7.698-7.726 (d, 1H, J=8.4 Hz), 7.641 (s, 1H), 7.211-7.239 (d, 2H, J=8.4 Hz), 7.164-7.198 (dd, 1H, J=8.4 Hz, 1.5 Hz), 6.503-6.532 (d, 2H, J=8.7 Hz), 5.178 (s, 2H), 2.358 (s, 3 Hs), 1.593 (s, 6H); MS: m/z 317 (M+).

Workup

  1. customAfter completion of reaction
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-fb3493830f934491b51253920e0dd5de
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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