Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86665065, compound

HRID 333347Notes

Reaction equation

HRID 333347 reaction equation
[Cl:1][C:2](=[CH2:12])[CH2:3][C:4]1([C:9]([OH:11])=O)[CH2:8][CH2:7][CH2:6][CH2:5]1.OC(C(F)(F)F)=O.[NH2:20][C@@H:21]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:30][CH:29]=1)[C:22]([N:24]([CH3:26])[CH3:25])=[O:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[C:31]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:32]=[CH:33][C:28]([CH2:27][C@H:21]([NH:20][C:9]([C:4]2([CH2:3][C:2]([Cl:1])=[CH2:12])[CH2:5][CH2:6][CH2:7][CH2:8]2)=[O:11])[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86665070HCID 86665070, compoundHCID 86665071HCID 86665071, compound

Product 1

HCID 86665065HCID 86665065, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-chloroallyl)cyclopentanecarboxylic acid (51 mg, 0.27 mmol) in DMF (1 mL) and CH2Cl2 (2 mL) was added (S)-2-amino-3-(biphenyl-4-yl)-N,N-dimethylpropanamide TFA salt (109 mg, 0.41 mmol) and TEA (0.19 mL, 1.35 mmol). To the mixture at room temperature was added HATU (154 mg, 0.41 mmol) and stirred at room temperature for 47 hours. The mixture was quenched with saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by TLC preparation plates using 70% EtOAc/heptane to give (S)—N-(3-(biphenyl-4-yl)-1-(dimethylamino)-1-oxopropan-2-yl)-1-(2-chloroallyl)cyclopentanecarboxamide (83 mg). HPLC retention time=1.76 minutes (condition B); MS (m+1)=439.1; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38-1.66 (m, 5H), 1.89-2.05 (m, 3H), 2.64 (d, J=15.3 Hz, 1H), 2.70 (d, J=15.3 Hz, 1H), 2.85 (s, 3H), 2.95 (s, 3H), 2.95 (dd, J=13.6, 6.1 Hz, 1H), 3.05 (dd, J=13.6, 6.1 Hz, 1H), 5.05 (s, 1H), 5.10 (s, 1H), 5.08-5.13 (m, 1H), 6.70 (d, J=8.1 Hz, 1H), 7.29 (d, J=8.1 Hz, 2H), 7.32-7.38 (m, 1H), 7.44 (t, J=7.7 Hz, 2H), 7.54 (d, J=8.1 Hz, 2H), 7.58-7.65 (m, 2H).

Workup

  1. customThe mixture was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by TLC preparation plates

Sources & evidence

ORD record
ord-655ca73fc3f34d7e9c884f458eb880b7
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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