Trifluoroacetic acid → 2-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamide

HRID 2421719노트

반응식

HRID 2421719 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[CH:18][N:19]=1)[C:5]([NH:7][O:8][CH2:9][C@H:10]1[CH2:14]OC(C)(C)[O:11]1)=[O:6].FC(F)(F)[C:31](O)=[O:32].CCOC(C)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[CH:18][N:19]=1)[C:5]([NH:7][O:8][CH2:9][CH:10]([OH:11])[CH2:14][CH2:31][OH:32])=[O:6]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 866291922-bromo-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-5-[(2-fluoro-4-iodophenyl)-amino]isonicotinamide

생성물 1

HCID 866291932-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamide수율 56%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamide was synthesized as described in General method 3: To a solution of 2-bromo-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-5-[(2-fluoro-4-iodophenyl)amino]-isonicotinamide (100.0 mg 0.18 mmol) in dichloromethane (1 ml) was added trifluoroacetic acid (1 ml) at RT. The reaction mixture was stirred at RT for 30 min, and monitored by TLC (Hex:EtOAc=1:1 and contain TEA). Upon completion, the volatiles were evaporated, and the residue was dissolved in dichloromethane, washed with 5% aq. NaHCO3 to get a precipitate. The residue was filtered, washed with water, and dried to get 53 mg (56%) of 2-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamide. LC/MS: [8.76 min, 541 (M+1)]

후처리

  1. custom2-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamide was synthesized
  2. customUpon completion, the volatiles were evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with 5% aq. NaHCO3
  5. customto get a precipitate
  6. filtrationThe residue was filtered
  7. washwashed with water
  8. customdried

출처 및 근거

ORD 기록
ord-c49f8d4004414eeda1ea9228d0f7cb49
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956191B2

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