Tetrahydrofuran → HCID 69655662, compound

HRID 11566

Reaction equation

HRID 11566 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:18]=[N:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2].C1COCC1>[Pd].CO>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:18]=[N:19][C:20]([CH2:23][NH2:24])=[CH:21][CH:22]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 69655660{2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

Product 1

HCID 69655662HCID 69655662, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a flask, 2920 mg (8.72 mmol) {2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester and 1000 mg Pd (10% on carbon) were placed under nitrogen and 10 ml THF and 120 ml methanol were added. The starting material was hydrogenated under atmospheric pressure and at rt for 3.5 h. The catalyst was filtered off. The solvent was evaporated and the residue was subjected to silica gel chromatography (toluene/isopropanol/NH3 (conc.) 16:20:1) to yield 2600 mg (7.6 mmol) {2-[(6-Aminomethyl-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester; exact MW [M+H] calc'd: 343.18; MW found [M+H]: 343.2.

Workup

  1. filtrationThe catalyst was filtered off
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5d0d19c1f38d4ac39a2931cfcb53fdfb
Source dataset
uspto-grants-2006_08
Patent number
US07098247B2

Linked notes

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