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

HRID 1921899ノート

反応式

HRID 1921899 の反応式
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

参加物

8

反応物 5

HCID 313Hydrochloric Acid2 回HCID 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
62.5 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0f972233af6b435b8ecc2427ec7d04e2
出典データセット
uspto-grants-2012_05
特許番号
US08173704B2

反応ノート

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