Diisopropylethylamine → N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-3-chloro-1-benzothiophene-2-carboxamide hydrochloride

HRID 335600

반응식

HRID 335600 반응식
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([OH:13])=O.CN(C(ON1N=[N:29][C:24]2[CH:25]=[CH:26][CH:27]=[N:28][C:23]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:38](N(CC)C(C)C)(C)[CH3:39]>CN(C=O)C>[ClH:1].[N:28]12[CH2:27][CH2:26][CH:25]([CH2:38][CH2:39]1)[C@H:24]([NH:29][C:11]([C:3]1[S:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=1[Cl:1])=[O:13])[CH2:23]2

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 3079643-Chloro-1-benzothiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 68432667N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-3-chloro-1-benzothiophene-2-carboxamide hydrochloride

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

254.2 mg (1.20 mmol) of 3-chloro-1-benzothiophene-2-carboxylic acid, 238 mg (1.20 mmol) of S-3-aminoquinuclidine dihydrochloride, 545.4 mg (1.43 mmol) of HATU, 556.1 mg (4.30 mmol) of N,N-diisopropylethylamine and 2.0 ml of DMF are reacted according to the general procedure (variant B). The reaction mixture is purified by preparative HPLC. The product is dissolved in 4M HCl in dioxane and then reconcentrated. 213 mg (49.9% of theory) of the title compound are obtained. The analytical data correspond to those of the racemate (example 14).

후처리

  1. customThe reaction mixture is purified by preparative HPLC
  2. dissolutionThe product is dissolved in 4M HCl in dioxane

출처 및 근거

ORD 기록
ord-21cf737d89e14819b20a626fb026af0c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884017B2

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