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Hydrochloric Acid → AV-608

HRID 1738914
ノート
印刷プレビュー

反応式

HRID 1738914 の反応式
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][C@H:9]1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)=[O:7].C(N(CC)CC)C.Cl.[N:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]([C:50](Cl)=[O:51])=[CH:42][CH:41]=1.Cl>C(Cl)Cl>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:50]([C:43]2[C:44]3[C:49](=[CH:48][CH:47]=[CH:46][CH:45]=3)[N:40]=[CH:41][CH:42]=2)=[O:51])[CH2:10][C@H:9]1[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)=[O:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2 回HCID 12373997Quinoline-4-carbonyl chloride hydrochloride2 回HCID 22869970((2R,4S)-4-amino-2-(4-chlorobenzyl)piperidin-1-yl)(3,5-bis(trifluoromethyl)phenyl)methanone

生成物 1

HCID 9917079AV-608

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

A solution of 1.70 g (3.65 mmol) of (2R,4S)-1-(3,5-bis-trifluoromethyl-benzoyl)-2-(4-chloro-benzyl)-piperidine4-amine and 1.5 ml (10.96 mmol) of triethylamine in 3 ml of methylene chloride is added dropwise at 0° C. to a solution of 0.915 g (4.01 mmol) of quinoline4-carboxylic acid chloride hydrochloride [Nicolai E, Gungor T, Goyard J, Cure G, Fouquet A, Teulon J M, Delchambre C, Cloarec A, Eur. J. Med. Chem., 1992, 27, 977] in 10 ml of methylene chloride. After 15 hours, a further 228 mg (1.0 mmol) of quinoline-4-carboxylic acid chloride hydrochloride and a further 0.1 ml (1.0 mmol) of triethylamine are added and the mixture is stirred for 3 hours. 1 N hydrochloric acid is added to the mixture which is then extracted with ethyl acetate. The organic phase is washed with 1 N sodium hydroxide solution and with brine, dried over sodium sulfate and concentrated. The residue is crystallised from toluene and yields the title compound in the form of white crystals. M.p. 204-207° C. (phase transition 135-140° C.); TLC: ethyl acetate: Rf =0.48, FD-MS: M+ =619(621). ##STR17##

後処理

  1. extractionis then extracted with ethyl acetate
  2. washThe organic phase is washed with 1 N sodium hydroxide solution and with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is crystallised from toluene

出典と根拠

ORDレコード
ord-a3fcaa192e8547f29980b83a61e3ae05
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05965562

反応ノート

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