Triethylamine → HCID 57884167, compound

HRID 1818085Notes

Reaction equation

HRID 1818085 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:33][CH2:32][C:27]2([C:21]3[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH:20]=3)[CH2:28][CH2:29][CH2:30][CH2:31]2)=[O:14])=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1364294-Benzylbenzoic 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 57884167HCID 57884167, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Benzyl-benzoic acid (21.2 mg, 0.100 mmol) and C-[1-(3,4-Dimethoxy-phenyl)-cyclopentyl]-methylamine (23.5 g, 0.100 mmol) were dissolved in acetonitrile (1 mL) containing triethylamine (41.8 μL, 0.300 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (38.0 mg, 0.100 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 (24.1 mg, 0.0561 mmol, 56.1%) ESI-MS m/z calc. 429.2, found 430.4 (M+1)+. Retention time of 3.75 minutes.

Workup

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

Sources & evidence

ORD record
ord-bd14822930124ed99d5b8fb24f59010e
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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