Phenethylamine → HCID 58276376, compound

HRID 70311Notes

Reaction equation

HRID 70311 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][CH:5]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([OH:31])=O)[CH:24]=3)=[CH:19][CH:18]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:66]([NH2:74])[CH2:67][C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1>CN(C=O)C>[CH3:32][C:2]1([CH3:1])[CH2:3][CH2:4][CH:5]([N:8]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:74][CH2:66][CH2:67][C:68]4[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=4)=[O:31])[CH:24]=3)=[CH:21][CH:22]=2)[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67160567HCID 67160567, compound

Product 1

HCID 58276376HCID 58276376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-[((4,4-dimethylcyclohexyl){[(1,1-dimethylethyl)oxy]carbonyl}amino)-methyl]-3-biphenylcarboxylic acid (0.100 g; 0.23 mmol) in DMF (2 mL) was added DIEA (0.035 mL; 0.25 mmol), and HATU (0.095 g; 0.25 mmol). The solution was aged 5 min at room temperature and phenethylamine (0.031 mL; 0.25 mmol) was added. After 45 min the mixture was partitioned between EtOAc and half-satd Na2CO3, layers were separated and the aqueous layer was extracted with EtOAc (×2). Combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum. LC/MS (method E) tR 1.19 min; m/z 541 (M+H).

Workup

  1. customAfter 45 min the mixture was partitioned between EtOAc and half-satd Na2CO3, layers
  2. customwere separated
  3. extractionthe aqueous layer was extracted with EtOAc (×2)
  4. washCombined organics were washed (water, brine)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-163eb6d37a094cabb3ef02a0ec0eae91
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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