Aniline → Diethyl [{2-[(phenylamino)carbonyl]-6-bromoquinolin-7-yl}(difluoro)methyl]phosphonate

HRID 523130Notes

Reaction equation

HRID 523130 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])([F:14])[F:13])[N:8]=[C:7]([C:23]([OH:25])=O)[CH:6]=[CH:5]2.CCN=C=NCCCN(C)C.[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:18]([O:17][P:15]([C:12]([C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([C:23]([NH:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:25])=[N:8]2)=[CH:3][C:2]=1[Br:1])([F:13])[F:14])(=[O:16])[O:20][CH2:21][CH3:22])[CH3:19]

Participants

6

Reactant 4

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 86638322HCID 86638322, compound

Product 1

HCID 86638324Diethyl [{2-[(phenylamino)carbonyl]-6-bromoquinolin-7-yl}(difluoro)methyl]phosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product of step 5 (109 mg) in 5 mL CH2Cl2 was added EDCI (96 mg), aniline (0.1 mL) and Hunig's base (0.1 mL). The solution was stirred at ambient temperature for 3 hours and after concentration and flash chromatography on silica with a gradient of 10-25% EtOAc/toluene the amide was obtained.

Workup

  1. concentrationafter concentration and flash chromatography on silica with a gradient of 10-25% EtOAc/toluene the amide
  2. customwas obtained

Sources & evidence

ORD record
ord-306b3dfd18bf4676bb738fa19a2ecdd9
Source dataset
uspto-grants-2016_05
Patent number
US09334295B2

Reaction notes

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