2,4-Dichlorobenzylamine → 3-Quinolinecarboxamide,8-chloro-1-cyclopropyl-n-[(2,4-dichlorophenyl)methyl]-6,7-difluoro-1,4-dihydro-4-oxo-

HRID 1011223

반응식

HRID 1011223 반응식
[Cl:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=O)[C:7]2=[O:18].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[Cl:54][C:55]1[CH:62]=[C:61]([Cl:63])[CH:60]=[CH:59][C:56]=1[CH2:57][NH2:58]>CN(C=O)C>[Cl:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:13][CH2:14]1)[CH:9]=[C:8]([C:15]([NH:58][CH2:57][C:56]1[CH:59]=[CH:60][C:61]([Cl:63])=[CH:62][C:55]=1[Cl:54])=[O:17])[C:7]2=[O:18]

참가 물질

5

반응물 3

HCID 14852,4-DichlorobenzylamineHCID 2724699PyBOPHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

생성물 1

HCID 577809783-Quinolinecarboxamide,8-chloro-1-cyclopropyl-n-[(2,4-dichlorophenyl)methyl]-6,7-difluoro-1,4-dihydro-4-oxo-

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

15.0 g of 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (for preparation see DE 3420743 or Y. Kimura et al. J. Med. Chem. 1994, 37 (20), 3344) are dissolved in 500 ml of DMF, and 31.3 g of PyBOP and 10.6 g of 2,4-dichlorobenzylamine are added. After one day the solvent is removed on a rotary evaporator and the residue is purified by flash chromatography on silica gel (toluene/ethyl acetate 95:5). 21.2 g (93% of theory) of the title compound are obtained.

후처리

  1. customAfter one day the solvent is removed on a rotary evaporator
  2. customthe residue is purified by flash chromatography on silica gel (toluene/ethyl acetate 95:5)

출처 및 근거

ORD 기록
ord-0df5073873de4cdcaf3721c12362310c
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977349B2

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