Hydrochloric Acid → Ethyl 5-{[2-(5-fluoro-2-{[4'-(trifluoromethyl)biphenyl-4-yl]-methoxy}phenyl)ethyl]amino}pentanoate

HRID 1921899노트

반응식

HRID 1921899 반응식
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[C:7]([CH2:9][CH2:10][NH2:11])[CH:8]=1.FC1C=CC(OCC2C=CC(C3C=CC(C(F)(F)F)=CC=3)=CC=2)=C(CCN)C=1.Cl.C(N(CC)CC)C.Br[CH2:67][CH2:68][CH2:69][CH2:70][C:71]([O:73][CH2:74][CH3:75])=[O:72]>O1CCOCC1.O>[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[C:7]([CH2:9][CH2:10][NH:11][CH2:67][CH2:68][CH2:69][CH2:70][C:71]([O:73][CH2:74][CH3:75])=[O:72])[CH:8]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric Acid2회HCID 8471TriethylamineHCID 84580Ethyl 5-bromovalerateHCID 579719282-(5-Fluoro-2-{[4'-(trifluoromethyl)-1,1'-biphenyl-4-yl]methoxy}phenyl)ethylamineHCID 674932422-(5-Fluoro-2-{[4'-(trifluoromethyl)biphenyl-4-yl]methoxy}phenyl)ethylamine hydrochloride

생성물 1

HCID 57971939Ethyl 5-{[2-(5-fluoro-2-{[4'-(trifluoromethyl)biphenyl-4-yl]-methoxy}phenyl)ethyl]amino}pentanoate

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
62.5 °C

실험 절차

13.8 g (30 mmol) of 2-(5-fluoro-2-{[4′-(trifluoromethyl)biphenyl-4-yl]methoxy}phenyl)ethylamine hydrochloride [obtainable by taking up the compound of Example 45A in a 1 M solution of hydrogen chloride in dioxane, reconcentrating the solution and drying the resulting residue] are introduced into 200 ml of DMF, mixed with 32.4 ml (0.23 mol) of triethylamine and heated to 60-65° C. At this temperature, 9.48 g (0.05 mol) of ethyl 5-bromovalerate are added dropwise, and the mixture is stirred for 12 hours. After cooling, the mixture is added to water, adjusted to pH 5 with 1 M hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is removed in vacuo. The resulting residue is purified by chromatography on silica gel (mobile phase: dichloromethane/methanol 10:1). 4.5 g (8.9 mmol, 18% of theory) of the title compound are obtained.

후처리

  1. customdrying the resulting residue]
  2. additionare introduced into 200 ml of DMF
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent is removed in vacuo
  7. customThe resulting residue is purified by chromatography on silica gel (mobile phase: dichloromethane/methanol 10:1)

출처 및 근거

ORD 기록
ord-0f972233af6b435b8ecc2427ec7d04e2
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173704B2

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