Dimethylformamide → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamide

HRID 335590

반응식

HRID 335590 반응식
[N+]([C:4]1[CH:15]=[CH:14][C:7]2[CH:8]=[C:9]([C:11]([OH:13])=O)[O:10][C:6]=2[CH:5]=1)([O-])=O.Cl.Cl.[NH2:18][C@@H:19]1[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1.CN(C([O:34][N:35]1N=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:64])C>>[N:21]12[CH2:26][CH2:25][CH:24]([CH2:23][CH2:22]1)[C@@H:19]([NH:18][C:11]([C:9]1[O:10][C:6]3[C:5]([N+:35]([O-:34])=[O:64])=[CH:4][CH:15]=[CH:14][C:7]=3[CH:8]=1)=[O:13])[CH2:20]2

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 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 DihydrochlorideHCID 131907266-Nitro-1-benzofuran-2-carboxylic acid

생성물 1

HCID 59341430N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamide

실험 절차

1040 mg (5.02 mmol) of 6-nitrobenzofuran-2-carboxylic acid, 1000 mg (5.02 mmol) of (R)-3-aminoquinuclidine dihydrochloride, 2290 mg (6.03 mmol) of HATU, 2250 mg (18.08 mmol) of N,N-diisopropylethylamine and 9 ml of DMF are reacted according to the general procedure (variant B). DMF is removed under reduced pressure. The product is taken up in 100 ml of 1N aqueous sodium hydroxide solution and extracted three times with in each case 50 ml of ethyl acetate. The combined organic phases are washed eight times with 1N aqueous sodium hydroxide solution and once with saturated sodium chloride solution and then dried over magnesium sulfate, and the solvent is removed under reduced pressure using a rotary evaporator. 1.34 g (79% of theory) of the title compound are obtained.

후처리

  1. customDMF is removed under reduced pressure
  2. extractionextracted three times with in each case 50 ml of ethyl acetate
  3. washThe combined organic phases are washed eight times with 1N aqueous sodium hydroxide solution
  4. dry with materialonce with saturated sodium chloride solution and then dried over magnesium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customa rotary evaporator

출처 및 근거

ORD 기록
ord-5f86c9294e3d4456bfa41008dad9777b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884017B2

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