Diphenylacetic Acid → HCID 2877827, compound

HRID 1818086Notes

Reaction equation

HRID 1818086 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:27]2([CH2:32][NH2:33])[CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].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>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:27]2([CH2:32][NH:33][C:8](=[O:10])[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:28][CH2:29][CH2:30][CH2:31]2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 8333Diphenylacetic AcidHCID 8471TriethylamineHCID 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 2877827HCID 2877827, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diphenyl-acetic acid (42.4 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 (13.3 mg, 0.0310 mmol, 15.5%) ESI-MS m/z calc. 429.2, found 430.2 (M+1)+. Retention time of 3.47 minutes.

Workup

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

Sources & evidence

ORD record
ord-3b9b2f6f96e2413e904d4c69ef6ce9e4
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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