Triethylamine → n-(4,6-Dimethylpyridin-2-yl)-2-methyl-6-{[7-(2-pyrrolidin-1-ylethoxy)quinolin-4-yl]oxy}-1-benzofuran-3-carboxamide

HRID 130675

Reaction equation

HRID 130675 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:13]=[C:12]([O:14][C:15]3[C:24]4[C:19](=[CH:20][C:21]([O:25][CH2:26][CH2:27][N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[CH:22][CH:23]=4)[N:18]=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:5]=2[C:6]=1[C:7](O)=[O:8].[CH3:33][C:34]1[CH:39]=[C:38]([CH3:40])[N:37]=[C:36]([NH2:41])[CH:35]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[CH3:33][C:34]1[CH:39]=[C:38]([CH3:40])[N:37]=[C:36]([NH:41][C:7]([C:6]2[C:5]3[CH:10]=[CH:11][C:12]([O:14][C:15]4[C:24]5[C:19](=[CH:20][C:21]([O:25][CH2:26][CH2:27][N:28]6[CH2:32][CH2:31][CH2:30][CH2:29]6)=[CH:22][CH:23]=5)[N:18]=[CH:17][CH:16]=4)=[CH:13][C:4]=3[O:3][C:2]=2[CH3:1])=[O:8])[CH:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 215072-Amino-4,6-dimethylpyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 597307642-Methyl-6-{[7-(2-pyrrolidin-1-ylethoxy)quinolin-4-yl]oxy}-1-benzofuran-3-carboxylic acid

Product 1

HCID 11226429n-(4,6-Dimethylpyridin-2-yl)-2-methyl-6-{[7-(2-pyrrolidin-1-ylethoxy)quinolin-4-yl]oxy}-1-benzofuran-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 121-G (43 mg), 4,6-dimethylpyridin-2-amine (25 mg), HATU (132 mg) and Et3N (47 mg) in DMF (2 ml) was heated to 70° C. for 4 hours. A small amount of product was seen by TLC. The reaction was allowed to stay for another 48 hours at room temperature. The reaction mixture was purified by HPLC (20-60% CH3CN/H2O, 0.1% AcOH over 30 min.) to give N-(4,6-dimethylpyridin-2-yl)-2-methyl-6-{[7-(2-pyrrolidin-1-ylethoxy)quinolin-4-yl]oxy}-1-benzofuran-3-carboxamide 121.

Workup

  1. customThe reaction mixture was purified by HPLC (20-60% CH3CN/H2O, 0.1% AcOH over 30 min.)

Sources & evidence

ORD record
ord-0f20892aafd2488698e9d892f4427034
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Linked notes

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