Triethylamine → HCID 178470901, compound

HRID 1791194Notes

Reaction equation

HRID 1791194 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[NH:13][C:12](=[O:14])[C:11]3=[C:15]([CH2:28][CH3:29])[N:16]=[C:17]([C@H:18]4[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19]4)[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:30]([O:34][CH2:35][CH3:36])(=[O:33])[CH:31]=[CH2:32].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:24]([C@@H:21]1[CH2:20][CH2:19][C@H:18]([C:17]2[N:10]3[C:11]([C:12](=[O:14])[NH:13][C:8]([C:4]4[CH:3]=[C:2](/[CH:32]=[CH:31]/[C:30]([O:34][CH2:35][CH3:36])=[O:33])[CH:7]=[CH:6][CH:5]=4)=[N:9]3)=[C:15]([CH2:28][CH3:29])[N:16]=2)[CH2:23][CH2:22]1)([CH3:25])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 178437646HCID 178437646, compound

Product 1

HCID 178470901HCID 178470901, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

740 mg (1.62 mmol) cis-2-(3-bromophenyl)-7-(4-tert-butylcyclohexyl)-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one (Example 27A), 1.6 g (16.2 mmol) ethyl acrylate, 327 mg (3.24 mmol) triethylamine and 227 mg (0.32 mmol) dichlorobis(triphenylphosphine)palladium(II) are stirred at 120° C. in 20 ml DMF in an argon atmosphere for 18 hours. After cooling down to room temperature, the mixture is filtrated over Celite, and the product is isolated by column chromatography or preparative HPLC.

Workup

  1. filtrationthe mixture is filtrated over Celite
  2. customthe product is isolated by column chromatography or preparative HPLC

Sources & evidence

ORD record
ord-706b6d16575d4ae18beff0d43bed92fb
Source dataset
uspto-grants-2006_07
Patent number
US07074790B2

Reaction notes

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