Dimethylformamide → HCID 59341385, compound

HRID 335576Notes

Reaction equation

HRID 335576 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=2[S:4][C:3]=1[C:14]([OH:16])=O.CN(C(ON1N=[N:32][C:27]2[CH:28]=[CH:29][CH:30]=[N:31][C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:41](N(CC)C(C)C)(C)[CH3:42].CN(C=O)C>CO>[N:31]12[CH2:30][CH2:29][CH:28]([CH2:41][CH2:42]1)[C@@H:27]([NH:32][C:14]([C:3]1[S:4][C:5]3[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=3[C:2]=1[Cl:1])=[O:16])[CH2:26]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 7398673-Chloro-6-nitro-1-benzothiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59341385HCID 59341385, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

427 mg (1.66 mmol) of 3-chloro-6-nitro-1-benzothiophene-2-carboxylic acid, 300 mg (1.51 mmol) of R-3-aminoquinuclidine dihydrochloride, 687.4 mg (1.81 mmol) of HATU, 701 mg (5.43 mmol) of N,N-diisopropylethylamine and 4.0 ml of DMF are reacted according to the general procedure. 20 ml of methanol and 4 g of Dowex WX2-200 are added, and the mixture is stirred at RT for 1 h. The mixture is filtered and washed successively with water, methanol, methanol/trifluoroacetic acid 9:1 and methanol/trifluoroacetic acid 1:1. Evaporation of the filtrate gives 270 mg (49% of theory) of the title compound.

Workup

  1. filtrationThe mixture is filtered
  2. washwashed successively with water, methanol, methanol/trifluoroacetic acid 9:1 and methanol/trifluoroacetic acid 1:1
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-2b219b02cf524bb0a83490fe95599b5d
Source dataset
uspto-grants-2014_11
Patent number
US08884017B2

Reaction notes

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