Ammonium Chloride → Trifluoroethylamine inhibitor, 1

HRID 1620911Notes

Reaction equation

HRID 1620911 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:33])[C@H:6]([CH2:29][CH:30]([CH3:32])[CH3:31])[NH:7][C@@H:8]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[C:9]([F:12])([F:11])[F:10])#[N:2].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:45]2N=CC=C[C:44]=2N=N1.Cl.C1(N)CC1.[Cl-].[NH4+]>CN(C=O)C.C(OCC)C.C(N(CC)CC)C>[C:1]([C:3]1([NH:4][C:5](=[O:33])[C@H:6]([CH2:29][CH:30]([CH3:31])[CH3:32])[NH:7][C@@H:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)[C:9]([F:10])([F:12])[F:11])[CH2:45][CH2:44]1)#[N:2]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9913088L-873724HCID 11708049Cyclopropylamine hydrochloride

Product 1

HCID 11283555Trifluoroethylamine inhibitor, 1

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of N-{(1S)-2,2,2-trifluoro-1-[4′-(methylsulfonyl)-1,1′-biphenyl-4-yl]ethyl}-L-leucine from Example 8 (0.83 g), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.78 g), cyclopropylamine hydrochloride (0.466 g) in DMF (18 mL) at 0° C. was added triethylamine (0.9 mL). The mixture was kept at room temperature for 48 hours and then poured into dilute aqueous ammonium chloride and diethyl ether. The ether layer was separated and the aqueous further extracted with diethylether. The combined ether extracts were washed with brine, dried with magnesium sulfate and the solvent was removed in vacuo. The residue was purified in SiO2 using ethyl acetate and hexanes (1:1) as eluant, followed by a swish in diethyl ether to yield the title compound.

Workup

  1. customThe ether layer was separated
  2. extractionthe aqueous further extracted with diethylether
  3. washThe combined ether extracts were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified in SiO2

Sources & evidence

ORD record
ord-bbb1242b0f9d4e2ea9ea3d1b7d8f47da
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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