2-Furancarboxylic acid → HCID 86611377, compound

HRID 1920566Notes

Reaction equation

HRID 1920566 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:26][P-:27]([F:32])([F:31])([F:30])([F:29])[F:28].N1CCOCC1.Cl.[Cl-].[NH2:41][CH2:42][CH2:43][N+:44]12[CH2:51][CH2:50][CH:47]([CH2:48][CH2:49]1)[C@@H:46]([C:52](=[O:67])[C:53]([OH:66])([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:45]2>CN(C=O)C>[F:26][P-:27]([F:32])([F:31])([F:30])([F:29])[F:28].[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:41][CH2:42][CH2:43][N+:44]12[CH2:49][CH2:48][CH:47]([CH2:50][CH2:51]1)[C@@H:46]([C:52](=[O:67])[C:53]([OH:66])([C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[CH2:45]2)=[O:8]

Participants

6

Reactant 4

HCID 69192-Furancarboxylic acidHCID 8083MorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86611371HCID 86611371, compound

Product 1

HCID 86611377HCID 86611377, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 2-furoic acid (91.5 mg, 8.21 mmol) and HATU (284 mg, 7.52 mmol) in DMF (7.5 ml) is added polymer bound morpholine, 2.5 mmol/g (1.36 g, 34.2 mmol). The reaction mixture is left to stand at room temperature for 15 minutes after which time, a solution comprising of (R)-1-(2-amino-ethyl)-3-(2-hydroxy-2,2-diphenyl-acetyl)-1-azonia-bicyclo[2.2.2]octane chloride hydrochloride [Example 180 i]] (310 mg, 6.84 mmol) in DMF (7.5 ml) is added. The reaction mixture is stirred at room temperature overnight. The reaction mixture is passed through a 2 g Isolute SPE (Al-B) cartridge. The filtrate is concentrated in vacuo and purification of the crude residue by chromatography on C18 silica, eluting with water:acetonitrile affords the title compound as a white solid.

Workup

  1. waitThe reaction mixture is left
  2. concentrationThe filtrate is concentrated in vacuo and purification of the crude residue by chromatography on C18 silica
  3. washeluting with water

Sources & evidence

ORD record
ord-aa7e72788cd04268a98547b7bb737197
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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