Water → HCID 10223066, compound

HRID 1934934Notes

Reaction equation

HRID 1934934 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][CH:18]=[C:17]([Br:21])[CH:16]=1.C(N(CC)CC)C.[CH3:29][C:30](=[CH2:34])[C:31](Cl)=[O:32].O>O1CCCC1>[Br:21][C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:31](=[O:32])[C:30]([CH3:34])=[CH2:29])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrile

Product 1

HCID 10223066HCID 10223066, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.5 g (1.48 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile and 0.194 g (1.92 mmol) of triethylamine in 6 ml tetrahydrofuran was added at 0° C., under nitrogen, with stirring, 0.21 g (1.92 mmol) of 2-methyl acryloyl chloride over a 10 minute period. The solution was stirred at room temperature overnight. The mixture was poured into water. The solid was collected and air dried. The solid was washed with boiling ethyl acetate and air dried giving 0.32 g of N-[4-[(3-bromophenyl)amino]-3-cyano-6-quinolinyl]-2-methyl-2-propenamide: mass spectrum (electrospray, m/e): M+H 407, 409.

Workup

  1. stirringThe solution was stirred at room temperature overnight
  2. customThe solid was collected
  3. customair dried
  4. washThe solid was washed with boiling ethyl acetate and air
  5. customdried

Sources & evidence

ORD record
ord-a3560494efed4fa4b53b2fd864684b54
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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