5-Methylpyrazin-2-amine → N-ethyl-N-methyl-5-(2-methyl-6-((5-methylpyrazin-2-yl)carbamoyl)benzofuran-4-yloxy)pyrimidine-2-carboxamide

HRID 1253623Notes

Reaction equation

HRID 1253623 reaction equation
[CH2:1]([N:3]([CH3:28])[C:4]([C:6]1[N:11]=[CH:10][C:9]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([CH3:22])[O:21][C:17]=3[CH:16]=[C:15]([C:23]([O:25]CC)=O)[CH:14]=2)=[CH:8][N:7]=1)=[O:5])[CH3:2].[CH3:29][C:30]1[N:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=1.[Cl-].C[Al+]C>>[CH2:1]([N:3]([CH3:28])[C:4]([C:6]1[N:11]=[CH:10][C:9]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([CH3:22])[O:21][C:17]=3[CH:16]=[C:15]([C:23](=[O:25])[NH:36][C:33]3[CH:32]=[N:31][C:30]([CH3:29])=[CH:35][N:34]=3)[CH:14]=2)=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 3132155-Methylpyrazin-2-amineHCID 16686359Dimethylalumanylium chlorideHCID 59483317Ethyl 4-(2-(ethyl(methyl)carbamoyl)pyrimidin-5-yloxy)-2-methylbenzofuran-6-carboxylate

Product 1

HCID 46916696N-ethyl-N-methyl-5-(2-methyl-6-((5-methylpyrazin-2-yl)carbamoyl)benzofuran-4-yloxy)pyrimidine-2-carboxamideYield 61%

Procedure

The title compound (5) was prepared by a method analogous to that described in Example 1 using ethyl 4-(2-(ethyl(methyl)carbamoyl)pyrimidin-5-yloxy)-2-methylbenzofuran-6-carboxylate (I-5a: 99 mg, 0.26 mmol), 5-methyl-2-aminopyrazine (84 mg, 0.77 mmol), dimethylaluminium chloride (1.29 mmol, 1M in hexane) and dimethylethere (4.5 mL) to afford N-ethyl-N-methyl-5-(2-methyl-6-((5-methylpyrazin-2-yl)carbamoyl)benzofuran-4-yloxy)pyrimidine-2-carboxamide (5: 70 mg, 61%) as an off white solid.

Workup

  1. customThe title compound (5) was prepared by a method analogous to

Sources & evidence

ORD record
ord-aaf02eb2c4f441629782af5d625d6eea
Source dataset
uspto-grants-2013_06
Patent number
US08455496B2

Reaction notes

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