Triethylamine → HCID 22466577, compound

HRID 1935006Notes

Reaction equation

HRID 1935006 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32].C(=O)(O)[O-].[Na+]>CN(C=O)C.C1COCC1>[C:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=1)=[CH:3][C:2]([NH:1][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:11][CH:10]=2)#[N:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 224665706-Amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile

Product 1

HCID 22466577HCID 22466577, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 1.00 g (3.37 mmol) 6-amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile in 2 ml DMF, added 12 ml THF, and chilled to 0° C. under N2. Added 517 μl (3.71 mmol) triethylamine and 310 μl (3.72 mmol) acryloyl chloride. Removed ice bath a 15 minutes. At 3.5 hours stripped solvent and slurried residue with dilute sodium bicarbonate. Collected solids, washed with water, and air dried. Boiled in ethyl acetate, collected solids and dried in vacuo, giving 332 mg of yellow solid: mass spectrum (electrospray m/e): M+H=351.1.

Workup

  1. customa 15 minutes
  2. customCollected solids
  3. washwashed with water, and air
  4. customdried
  5. customcollected solids
  6. customdried in vacuo

Sources & evidence

ORD record
ord-03e014cf13c043c4b6ffcebe8421996a
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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