Triethylamine → HCID 136090311, compound

HRID 130661Notes

Reaction equation

HRID 130661 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:25]=[CH:24][C:16]4[C:17]([C:21]([OH:23])=O)=[C:18]([CH3:20])[O:19][C:15]=4[CH:14]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:37]=[CH:38][CH:39]=[N:40]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C1(N)CC1>CN(C=O)C.O>[CH:39]1([NH:40][C:21]([C:17]2[C:16]3[CH:24]=[CH:25][C:13]([O:12][C:6]4[C:5]5[C:10](=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=5)[N:9]=[CH:8][CH:7]=4)=[CH:14][C:15]=3[O:19][C:18]=2[CH3:20])=[O:23])[CH2:37][CH2:38]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1360903156-[(7-Hydroxy-4-quinolinyl)oxy]-2-methyl-3-benzofurancarboxylic acid

Product 1

HCID 136090311HCID 136090311, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 90-E (1.6 g, 4.8 mmol), HATU (2.1 g, 5.7 mmol) and triethylamine (970 mg, 9.6 mmol) in DMF (10 ml) was stirred at room temperature for 20 minutes. To the solution was added cyclopropanamine 90-F (547 mg, 9.6 mmol). The reaction mixture was stirred for 30 minutes, poured into water and extracted with EtOAc. Silica gel column chromatography using 5% MeOH in CH2Cl2 yield N-cyclopropyl-6-[(7-hydroxyquinolin-4-yl)oxy]-2-methyl-1-benzofuran-3-carboxamide 90-G (1.4 g, 77% yield) as a solid.

Workup

  1. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-37efa474335145d2b2e16d393078cb9e
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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