Diisopropylethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-nitro-1-benzofuran-2-carboxamide

HRID 15460

反応式

HRID 15460 の反応式
[N+:1]([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-:3])=[O:2].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(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>[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[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:15]=[CH:14][C:7]=3[CH:8]=1)=[O:13])[CH2:20]2

参加物

6

反応物 4

HCID 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

生成物 1

HCID 59341358N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-nitro-1-benzofuran-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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 15 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 dried over magnesium sulfate and the solvent is removed under reduced pressure using a rotary evaporator. The reaction mixture is taken up in methanol and, together with acidic ion exchange resin (Dowex WX2-200), stirred for about 40 min. The loaded ion exchange is washed six times with in each case 100 ml of methanol. The product is then eluted with methanol/triethylamine 99:1 to 90:10. The solvent is removed under reduced pressure. The product is dried over magnesium sulfate. 1.75 g (99% of theory) of the title compound are isolated.

後処理

  1. customDMF is removed under reduced pressure
  2. extractionextracted three times with in each case 50 ml of ethyl acetate
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customa rotary evaporator
  6. washThe loaded ion exchange is washed six times with in each case 100 ml of methanol
  7. washThe product is then eluted with methanol/triethylamine 99:1 to 90:10
  8. customThe solvent is removed under reduced pressure
  9. dry with materialThe product is dried over magnesium sulfate

出典と根拠

ORDレコード
ord-450167238e4f4113840f7e2e746918bb
出典データセット
uspto-grants-2010_06
特許番号
US07732477B2

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