Triethylamine → Ethyl 2-(5-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)-2-oxopyridin-1(2H)-yl)ethylcarbamate

HRID 869992Notes

Reaction equation

HRID 869992 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:16]=[C:15]([NH:17][C:18]([C:20]3([C:23]4[CH:33]=[CH:32][C:26]5[O:27][C:28]([F:31])([F:30])[O:29][C:25]=5[CH:24]=4)[CH2:22][CH2:21]3)=[O:19])[CH:14]=[CH:13][C:12]=2[CH3:34])=[CH:5]1.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37].C(N(CC)CC)C>CN(C)C=O>[F:30][C:28]1([F:31])[O:27][C:26]2[CH:32]=[CH:33][C:23]([C:20]3([C:18]([NH:17][C:15]4[N:16]=[C:11]([C:6]5[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH2:3][CH2:2][NH:1][C:36](=[O:37])[O:38][CH2:39][CH3:40])[CH:5]=5)[C:12]([CH3:34])=[CH:13][CH:14]=4)=[O:19])[CH2:22][CH2:21]3)=[CH:24][C:25]=2[O:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 71053044N-(6-(1-(2-aminoethyl)-6-oxo-1,6-dihydropyridin-3-yl)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Product 1

HCID 71053043Ethyl 2-(5-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)-2-oxopyridin-1(2H)-yl)ethylcarbamateYield 25.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask containing N-(6-(1-(2-aminoethyl)-6-oxo-1,6-dihydropyridin-3-yl)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (36 mg, 0.08 mmol), ethyl chloroformate (10 mg, 0.09 mmol), and triethylamine (32 μL, 0.23 mmol) was added N,N-dimethyl formamide (1 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered and purified by reverse-phase preparative liquid chromatography to give the product (11 mg, 25%). ESI-MS m/z calc. 540.18. found 541.7 (M+1)+. Retention time 1.72 minutes.

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record
ord-439faaf04f6e415da64855b9918e5cb7
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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