Cyclopropanecarboxylic acid → HCID 178522512, compound

HRID 1639560Notes

Reaction equation

HRID 1639560 reaction equation
F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C.C(N(C(C)C)CC)(C)C.[CH:34]1([C:37]([OH:39])=O)[CH2:36][CH2:35]1.[Cl:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([Cl:47])[C:42]=1[S:48]([O:51][C:52]1[CH:61]=[CH:60][C:55]2[NH:56][C:57]([NH2:59])=[N:58][C:54]=2[CH:53]=1)(=[O:50])=[O:49]>CN(C)C=O.O.C(#N)C.C(OCC)C>[Cl:47][C:43]1[CH:44]=[CH:45][CH:46]=[C:41]([Cl:40])[C:42]=1[S:48]([O:51][C:52]1[CH:61]=[CH:60][C:55]2[NH:56][C:57]([NH:59][C:37]([CH:34]3[CH2:36][CH2:35]3)=[O:39])=[N:58][C:54]=2[CH:53]=1)(=[O:50])=[O:49]

Participants

9

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178508208HCID 178508208, compound

Product 1

HCID 178522512HCID 178522512, compoundYield 37.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 468 mg of N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylmethanaminium hexafluorophosphate in 5 cm3 of dimethylformamide are added 159 mg of diisopropylethylamine and 106 mg of cyclopropanecarboxylic acid. After stirring the reaction medium for one hour at a temperature in the region of 20° C., 220 mg of 2-amino-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained. The mixture is stirred overnight at a temperature in the region of 20° C. The reaction medium is diluted with 50 cm3 of water and the insoluble material is filtered off, washed with three times 5 cm3 of water, filtered off by suction and dried under a stream of air. The solid obtained is solidified in 10 cm3 of a mixture of diethyl ether and acetonitrile (7/3 by volume) and then filtered off by suction, washed with three times 2 cm3 of diethyl ether and dried under reduced pressure over phosphorus pentoxide. 98 mg of 2-[(cyclopropylcarbonyl)amino]-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained in the form of a white powder, the characteristics of which are as follows:

Workup

  1. customare obtained
  2. filtrationthe insoluble material is filtered off
  3. washwashed with three times 5 cm3 of water
  4. filtrationfiltered off by suction
  5. customdried under a stream of air
  6. customThe solid obtained
  7. filtrationfiltered off by suction
  8. washwashed with three times 2 cm3 of diethyl ether
  9. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-7e55a52ecd6a42aa8e68d032a2fd6795
Source dataset
uspto-grants-2012_02
Patent number
US08110571B2

Reaction notes

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