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

HRID 15466
Notes
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Reaction equation

HRID 15466 reaction equation
[Br:1][C:2]1[C:10]2[O:9][C:8]([C:11]([OH:13])=O)=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.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>CO>[N:28]12[CH2:27][CH2:26][CH:25]([CH2:38][CH2:39]1)[C@@H:24]([NH:29][C:11]([C:8]1[O:9][C:10]3[C:2]([Br:1])=[CH:3][CH:4]=[CH:5][C:6]=3[CH:7]=1)=[O:13])[CH2:23]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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 179826517-Bromobenzofuran-2-carboxylic acid

Product 1

HCID 59341359N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzofuran-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

300 mg (1.25 mmol) of 7-bromobenzofuran-2-carboxylic acid, 248 mg (1.25 mmol) of R-3-aminoquinuclidine dihydrochloride, 568 mg (1.494 mmol) of HATU, 579 mg (4.48 mmol) of N,N-diisopropylethylamine and 5 ml of DMF are reacted according to the general procedure (variant B). The product is taken up in methanol and, together with acidic ion exchange resin (Dowex WX2-200), shaken for about 30 min. The loaded ion exchanger is washed with DMF, water, methanol, dichloromethane, water, DMF and once again with methanol. The product is eluted with methanol/triethylamine 90:10. The solvent is removed under reduced pressure using a rotary evaporator. The pre-purified product is purified by preparative HPLC. 320 mg (74% of theory) of the title compound are isolated.

Workup

  1. washThe loaded ion exchanger is washed with DMF, water, methanol, dichloromethane, water, DMF and once again with methanol
  2. washThe product is eluted with methanol/triethylamine 90:10
  3. customThe solvent is removed under reduced pressure
  4. customa rotary evaporator
  5. customThe pre-purified product is purified by preparative HPLC

Sources & evidence

ORD record
ord-39eaf1af717143088d0143d273d4d422
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732477B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes