Diisopropylethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-bromo-1-benzothiophene-2-carboxamide hydrochloride

HRID 658180

반응식

HRID 658180 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][C:6]=2[CH:13]=1.[ClH:14].Cl.[NH2:16][C@@H:17]1[CH:22]2[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]2)[CH2:18]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[ClH:14].[N:19]12[CH2:24][CH2:23][CH:22]([CH2:21][CH2:20]1)[C@@H:17]([NH:16][C:10]([C:8]1[S:9][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][C:6]=3[CH:7]=1)=[O:12])[CH2:18]2

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 7377375-Bromo-benzo(b)thiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

생성물 1

HCID 10287550N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-bromo-1-benzothiophene-2-carboxamide hydrochloride

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

133.7 mg (0.52 mmol) of 5-bromo-1-benzothiophene-2-carboxylic acid, 155.4 mg (0.78 mmol) of (R)-3-aminoquinuclidine dihydrochloride, 296.7 mg (0.78 mmol) of HATU, 369.8 mg (2.86 mmol) of N,N-diisopropylethylamine and 1.5 ml of DMF are reacted according to the general procedure (variant A). The reaction mixture is purified by preparative HPLC. The product is dissolved in acetonitrile, and an excess of 1N hydrochloric acid is added. The solvent is then removed. 175 mg (84% of theory) of the title compound are isolated.

후처리

  1. customThe reaction mixture is purified by preparative HPLC
  2. dissolutionThe product is dissolved in acetonitrile
  3. additionan excess of 1N hydrochloric acid is added
  4. customThe solvent is then removed

출처 및 근거

ORD 기록
ord-074f6e623c954eafa51f47776a3c1369
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076355B2

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