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

HRID 15462

반응식

HRID 15462 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-305ee33818314552b45ed63c07444bb1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732477B2

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