HCID 22466694, compound → HCID 10202344, compound

HRID 612019Notes

Reaction equation

HRID 612019 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:32])[C:21]#[C:22][CH2:23][O:24][Si](C(C)(C)C)(C)C)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:33]#[N:34])[CH:5]=[CH:6][CH:7]=1>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:32])[C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:33]#[N:34])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 22466694HCID 22466694, compound

Product 1

HCID 10202344HCID 10202344, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

N-[4-[(3-Bromophenyl)amino]-3-cyano-6-quinolinyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-butynamide (0.120 g, 0.224 mmol) was dissolved in a 25 ml solution (acetic acid:tetrahydrofuran:water=3:1:1) and stirred overnight at 25° C. The reaction was poured into ethyl acetate and washed with saturated sodium bicarbonate and brine. The product was collected, washed with ethyl acetate, and dried in vacuo to give 0.085 g of yellow solid (90%); ESMS m/z 421.2 (M+H+); mp 253-254° C.(dec).

Workup

  1. washwashed with saturated sodium bicarbonate and brine
  2. customThe product was collected
  3. washwashed with ethyl acetate
  4. customdried in vacuo

Sources & evidence

ORD record
ord-75a97eff1d6948d7b4c10d8ba4c392c4
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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