HCID 69850196, compound → HCID 178510311, compound

HRID 276842Notes

Reaction equation

HRID 276842 reaction equation
C(O[C:4](=[O:26])[C:5]([C:24]#[N:25])=[CH:6][NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:12][CH:13]=1)C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[OH:26][C:4]1[C:9]2[C:8](=[CH:13][CH:12]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[N:10]=2)[N:7]=[CH:6][C:5]=1[C:24]#[N:25]

Participants

3

Reactant 1

HCID 69850196HCID 69850196, compound

Product 1

HCID 178510311HCID 178510311, compound

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Conditions

Temperature
260 °C

Procedure

A solution of 2-cyano-3-[6-(3-morpholin-4-yl-propoxy)-pyridin-3-ylamino]-acrylic acid ethyl ester (10 g) in Dowtherm (200 ml) was heated at 260° C. (internal temperature) under argon. During the first 8 hrs of heating, ethanol was removed through distillation head attached to apparatus. Then, the reaction mixture was heated at 260° C. for an additional 5 hrs. After cooling, the mixture was poured into hexanes. The solid was collected, and suspended in a mixture of CH2Cl2 and MeOH (ca 5:1). The black undissolved solid was removed, and the filtrate was diluted with ether. The yellowish brown solid was precipitated, collected, and dried to give the title compound mass spectrum (electrospray, m/e): 315.0 (M+H); IR cm-1: 2227, 1666, 1630; H-NMR δ(DMSO-d6): 1.88-1.90 (2H, m), 2.26-2.29 (6H, m), 2.51 (2H, m), 3.49 (2H,m), 4.34 (2H, m), 6.852 (1H, d, C7-H), 8.147 (1H, d, C8-H) 8.715 (1H, s, C2-H), 11.2 (1H, bs, OH).

Workup

  1. temperatureDuring the first 8 hrs of heating
  2. customethanol was removed through distillation head
  3. temperatureAfter cooling
  4. additionthe mixture was poured into hexanes
  5. customThe solid was collected
  6. additionsuspended in a mixture of CH2Cl2 and MeOH (ca 5:1)
  7. customThe black undissolved solid was removed
  8. additionthe filtrate was diluted with ether
  9. customThe yellowish brown solid was precipitated
  10. customcollected
  11. customdried

Sources & evidence

ORD record
ord-a52c91ac2d5844e896a3aacab78f6c40
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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