Triethylamine → HCID 57884141, compound

HRID 1818087Notes

Reaction equation

HRID 1818087 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([OH:9])=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:26]2([CH2:31][NH2:32])[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(#N)C>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:26]2([CH2:31][NH:32][C:7]([C:6]3[CH:5]=[C:4]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[O:3][C:2]=3[CH3:1])=[O:9])[CH2:27][CH2:28][CH2:29][CH2:30]2)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 7365162-Methyl-5-phenyl-3-furoic acidHCID 739193STK362959HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57884141HCID 57884141, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methyl-5-phenyl-furan-3-carboxylic acid (40.4 mg, 0.200 mmol) and C-[1-(3,4-Dimethoxy-phenyl)-cyclopentyl]-methylamine (47.1 g, 0.200 mmol) were dissolved in acetonitrile (1 mL) containing triethylamine (83.6 μL, 0.600 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (76.0 mg, 0.200 mmol) was added and the solution was allowed to stir for 16 hours. The mixture was then purified by reverse phase preparative liquid chromatography to yield the pure product (17.0 mg, 0.0405 mmol, 20.3%) ESI-MS m/z calc. 419.2, found 420.4 (M+1)+. Retention time of 3.62 minutes.

Workup

  1. customThe mixture was then purified by reverse phase preparative liquid chromatography

Sources & evidence

ORD record
ord-b6e23f0c734a4c5988d9240fba13f41e
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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