Ethylamine → HCID 67116995, compound

HRID 444702Notes

Reaction equation

HRID 444702 reaction equation
[C:1](/[C:3](=[C:9](\[C:18]1[C:19]([CH:24]([F:26])[F:25])=[N:20][N:21]([CH3:23])[CH:22]=1)/[NH:10][CH:11]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)[CH3:12])/[C:4]([O:6]CC)=O)#[N:2].[CH2:27]([NH2:29])[CH3:28].[CH3:30][Al](C)C>C1(C)C=CC=CC=1>[C:1](/[C:3](=[C:9](\[C:18]1[C:19]([CH:24]([F:26])[F:25])=[N:20][N:21]([CH3:23])[CH:22]=1)/[NH:10][CH:11]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)[CH3:12])/[C:4]([NH:29][CH:27]1[CH2:30][CH2:28]1)=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 16682925TrimethylaluminumHCID 67237684HCID 67237684, compound

Product 1

HCID 67116995HCID 67116995, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl (2Z)-2-cyano-3-[3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl]-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylate (0.122 g, 0.32 mmol, 1 eq.) in 3 ml of toluene was treated with ethylamine (1 M solution in tetrahydrofurane, 0.96 ml, 0.96 mmol, 3 eq.) and AlMe3 (1 M solution in toluene, 0.96 ml, 0.96 mmol, 3 eq.). The reaction was microwaved at 110° C. for 1800s (fixed hold, high absorption). The reaction was quenched with aqueous saturated NH4Cl and extracted with ethylacetate. The organic layers were combined and dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel to give (2Z)-2-cyano-N-cyclopropyl-3-[3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl]-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylamide (0.068 g, 51% yield) as a mixture of atropoisomers.

Workup

  1. customThe reaction was quenched with aqueous saturated NH4Cl
  2. extractionextracted with ethylacetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-05ba539475484290bf979b5767a8e5f8
Source dataset
uspto-grants-2013_07
Patent number
US08476197B2

Reaction notes

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