Ethylenediamine → HCID 86584826, compound

HRID 1835353Notes

Reaction equation

HRID 1835353 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C:13]([CH3:40])([CH3:39])[C:14]([N:16]([CH3:38])[C:17]2[CH:18]=[N:19][C:20]([C:30]#[C:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N)CN>[Pd].CO>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([C:13]([CH3:40])([CH3:39])[C:14]([N:16]([CH3:38])[C:17]2[CH:18]=[N:19][C:20](/[CH:30]=[CH:31]\[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[O:15])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 23502848HCID 23502848, compound

Product 1

HCID 86584826HCID 86584826, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 100 mg (0.198 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(6-phenylethynyl-4-o-tolyl-pyridin-3-yl)-isobutyramide (Example 72), 10 mg (0.17 mmol) ethylenediamine and 1 mg 10% palladium on carbon in 2 ml methanol was stirred at room temperature under an atmosphere of hydrogen gas for 8 h. The reaction mixture was filtered and concentrated. Column chromatography afforded 28 mg (24%) of the title compound as an orange viscous oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-df20ebfbdc0644d29d344b5b7a99d2c2
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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