HCID 10310224, compound → HCID 22343607, compound

HRID 583823Notes

Reaction equation

HRID 583823 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:11]([F:22])[CH:10]=2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=2)[N:3]=1.[H][H]>[Pd].C(O)C.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)=[C:11]([F:22])[CH:10]=2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=2)[N:3]=1

Participants

6

Reactant 2

HCID 10310224HCID 10310224, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22343607HCID 22343607, compoundYield 64.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A dry flask under argon was charged with 10% palladium on carbon (20 mg). A solution of N-[2-amino-6-(3-nitrophenyl)-4-pyrimidinyl]-N-[3-fluoro-4-(4-pyridinylsulfanyl)phenyl]amine (Example 20, 200 mg, 0.46 mmol) in ethanol (12 mL) and EtOAc (1 mL) was added via syringe through a septa to the palladium on carbon. The flask was then fitted with a hydrogen balloon and stirred at room temperature for 48 h. At this time the palladium was filtered through a pad of Celite®. The filtrate was coated on silica and purified on the MPLC (Biotage) with 2-8% MeOH in CH2Cl2 to afford the desired product as a solid (120 mg, 64%). TLC (6% MeOH in CH2Cl2) Rf0.26; MS (ES) 405 [M+H]+; 1H-NMR (DMSO-d6) δ 5.22 (bs, 2H), 6.45 (s, 1H), 6.49 (bs, 2H) 6.62-6.65 (m, 1H), 6.98 (d, J=6.4 Hz, 2H), 7.02-7.16 (m, 3H), 7.43-7.55 (m, 2H), 8.30-8.35 (m, 3H), 9.75 (bs, 1H).

Workup

  1. filtrationAt this time the palladium was filtered through a pad of Celite®
  2. custompurified on the MPLC (Biotage) with 2-8% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-f04ae98590ef467f804fc414987704e8
Source dataset
uspto-grants-2005_08
Patent number
US06924290B2

Reaction notes

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