Triethylamine → HCID 68586091, compound

HRID 1942907Notes

Reaction equation

HRID 1942907 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:13]([O:23][CH3:24])[CH:12]=2)[N:3]=1.C(N(CC)CC)C.[C:32]([O:35][CH2:36]C)(=[O:34])C>CO.ClCCl.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH3:36][O:35][C:32]([C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:13]([O:23][CH3:24])[CH:12]=2)[N:3]=1)=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86640783(4-Chloro-6-methoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

Product 1

HCID 68586091HCID 68586091, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 86640788HCID 86640788, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of (4-chloro-6-methoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (0.35 g, 1.0 mmol) in a mixture of 7 ml methanol and 3.5 ml ethyl acetate was treated with triethylamine (0.21 ml, 1.5 mmol) and tris(dibenzylideneacetone) dipalladium dichloromethane-complex (70 mg, 0.09 mmol). The mixture was transferred to an autoclave, flushed with carbon monoxide and hold 20 hours at 80° C. under a pressure of 5 bar of carbon monoxide. After cooling and evacuating the carbon monoxide, the mixture was concentrated to about 2 ml and diluted again with a mixture of ethyl acetate/methanol 9:1 v/v. The title compound precipitated as an intensely yellow solid after cooling in the refrigerator for 17 hours. Yield=55%.

Workup

  1. customflushed with carbon monoxide
  2. temperatureAfter cooling
  3. customevacuating the carbon monoxide
  4. concentrationthe mixture was concentrated to about 2 ml
  5. additiondiluted again with a mixture of ethyl acetate/methanol 9:1 v/v
  6. customThe title compound precipitated as an intensely yellow solid
  7. temperatureafter cooling in the refrigerator for 17 hours

Sources & evidence

ORD record
ord-654a6ce1a6694cbfb7aa0244c2e09420
Source dataset
uspto-grants-2013_03
Patent number
US08389717B2

Reaction notes

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