Tetrahydrofuran → HCID 22466677, compound

HRID 1935149Notes

Reaction equation

HRID 1935149 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]([CH:21]([CH3:23])[CH3:22])[CH:16]=1.[CH2:24]1C[O:27][CH2:26][CH2:25]1.C(N(CC)CC)C.C(Cl)(=O)C=C>CN(C=O)C>[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][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[CH:16]=1)=[CH:3][C:2]([NH:1][C:26](=[O:27])[CH:25]=[CH2:24])=[CH:11][CH:10]=2)#[N:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 22466682HCID 22466682, compound

Product 1

HCID 22466677HCID 22466677, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 1.00 g (3.31 mmol) 6-amino-4-[(3-isopropylphenyl)amino]-3-quinolinecarbonitrile in 2.0 ml hot DMF, added 12 ml THF, and chilled to 0° C. under N2. Added 507 μl (3.64 mmol) triethylamine and 303 μl (3.64 mmol) acryloyl chloride. Removed ice bath at 15 minutes and at 1 hour stripped solvent. Slurried residue with dilute sodium bicarbonate, collected solids and washed with water. Recrystallized from ethyl acetate and dried in vacuo, giving 366 mg of orange solid: mass spectrum (electrospray m/e): M+H=357.1.

Workup

  1. waitat 1 hour stripped
  2. customSlurried residue with dilute sodium bicarbonate, collected solids
  3. washwashed with water
  4. customRecrystallized from ethyl acetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2e112d9c7d86479f99532a5967f2cd7f
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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