Triethylamine → HCID 58033085, compound

HRID 533975Notes

Reaction equation

HRID 533975 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[O:11][C:10]([NH2:12])=[N:9][CH:8]=2)=[CH:4][CH:3]=1.[CH:15]1([CH:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([OH:24])=O)[CH2:20][CH2:19][CH2:18][CH2:17]C1.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>CN(C)C=O>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[O:11][C:10]([NH:12][C:22](=[O:24])[CH:21]([CH:15]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97942alpha-Cyclohexylphenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58033070HCID 58033070, compound

Product 1

HCID 58033085HCID 58033085, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(4-Chloro-benzyl)-oxazol-2-ylamine (42 mg, 0.20 mmol) and cyclohexyl-phenyl-acetic acid (44 mg, 0.20 mmol) were dissolved in N,N-dimethylformamide (1 mL) containing triethylamine (84.1 μL, 0.600 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (84 mg, 0.22 mmol) was added and the solution was allowed to stir for 16 hours. The crude product was purified by reverse-phase preparative liquid chromatography (9.6 mg, 0.023 mmol, 12%). ESI-MS m/z calc. 408.9. found 409.4 (M+1)+ Retention time 3.76 minutes.

Workup

  1. customThe crude product was purified by reverse-phase preparative liquid chromatography (9.6 mg, 0.023 mmol, 12%)

Sources & evidence

ORD record
ord-a55f2214580e4d95873149b9c6fb6512
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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