Perfluorophenyl isocyanate → HCID 21101668, compound

HRID 1353442Notes

Reaction equation

HRID 1353442 reaction equation
[F:1][C:2]1[C:7]([N:8]=[C:9]=[O:10])=[C:6]([F:11])[C:5]([F:12])=[C:4]([F:13])[C:3]=1[F:14].CCN(C(C)C)C(C)C.[Cl:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)=[CH:30][C:31]([NH2:35])=[N:32]2)=[CH:27][CH:26]=1>CN(C=O)C>[NH2:35][C:31]1[CH:30]=[C:29]([N:36]2[CH2:37][CH2:38][N:39]([C:9]([NH:8][C:7]3[C:2]([F:1])=[C:3]([F:14])[C:4]([F:13])=[C:5]([F:12])[C:6]=3[F:11])=[O:10])[CH2:40][CH2:41]2)[C:28]2[C:33](=[CH:34][C:25]([Cl:24])=[CH:26][CH:27]=2)[N:32]=1

Participants

5

Reactant 3

HCID 74125Perfluorophenyl isocyanateHCID 81531DiisopropylethylamineHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamine

Product 1

HCID 21101668HCID 21101668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of pentafluorophenyl isocyanate (0.03 mL, 0.23 mmol) and iPr2NEt (0.05 mL, 0.29 mmol) in DMF (1 mL), a hot solution of 7-chloro-4-(1-piperazinyl)-2-quinolinamine (50 mg, 0.19 mmol) in DMF (2 mL) was added. After stirring at rt overnight, the mixture was poured into ice-water. The solid was collected by filtration and re-dissolved in CH2Cl2-MeOH, then purified by preparative TLC (CH2Cl2-MeOH, 9:1) affording the product as a light yellow solid. LC-MS: 472 (M++1). 1HNMR (DMSO-d6) δ 3.02 (br.s, 4H), 3.70 (br.s, 4H), 6.28 (s, 1H), 6.50 (s, 2H), 7.10 (d, 1H), 7.39 (s, 1H), 7.78 (d, 1H), 8.80 (s, 1H).

Workup

  1. filtrationThe solid was collected by filtration
  2. dissolutionre-dissolved in CH2Cl2-MeOH
  3. custompurified by preparative TLC (CH2Cl2-MeOH, 9:1)

Sources & evidence

ORD record
ord-338c4b5a27f043c59a84d6f9064767d7
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

Loading…