Triethylamine → HCID 44409596, compound

HRID 1163064Notes

Reaction equation

HRID 1163064 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:15])=[C:7]2[N:12]([CH:13]=1)[N:11]=[CH:10][N:9]=[C:8]2Cl)=[O:4].[CH3:16][C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([OH:26])=[CH:21][CH:20]=2.C(N(CC)CC)C>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:15])=[C:7]2[N:12]([CH:13]=1)[N:11]=[CH:10][N:9]=[C:8]2[O:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH3:16])=[CH:25]2)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 833362-methyl-1H-indol-5-olHCID 21945969Methyl 4-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

Product 1

HCID 44409596HCID 44409596, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-chloro-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester (0.5 g, 2.22 mmol) and 2-methyl-5-hydroxyindole (424 mg, 2.9 mmol) under argon in acetonitrile (10.0 mL) was added triethylamine (6.65 mmol, 0.93 mL). After stirring the mixture at room temperature for 17 h. solvent was removed under vacuum and the residue was chromatographed on silica gel eluting with 20-30% ethyl acetate (gradient) in hexanes. The solvent was removed in vacuo to obtain 5-methyl-4-(2-methyl-1H-indol-5-yloxy)-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester as a white solid (0.58 g, 85%). LC/MS; (M+H)+=337.2

Workup

  1. customwas removed under vacuum
  2. customthe residue was chromatographed on silica gel eluting with 20-30% ethyl acetate (gradient) in hexanes
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4cc158851cee4019b5a6ce0ddac08df8
Source dataset
uspto-grants-2010_10
Patent number
US07820814B2

Reaction notes

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