Triethylamine → HCID 67050788, compound

HRID 1498569Notes

Reaction equation

HRID 1498569 reaction equation
C[N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+].C(N(CC)CC)C.FC(F)(F)C(O)=O.[F:41][C:42]([F:70])([F:69])[CH2:43][N:44]1[C:48]([C:49]2[N:58]=[C:57]3[N:51]([CH2:52][CH2:53][O:54][C:55]4[CH:62]=[C:61]([NH:63][CH:64]([CH3:68])[C:65]([OH:67])=O)[CH:60]=[CH:59][C:56]=43)[CH:50]=2)=[N:47][CH:46]=[N:45]1>CN(C=O)C>[F:41][C:42]([F:69])([F:70])[CH2:43][N:44]1[C:48]([C:49]2[N:58]=[C:57]3[C:56]4[CH:59]=[CH:60][C:61]([NH:63][C@@H:64]([CH3:68])[C:65]([NH2:2])=[O:67])=[CH:62][C:55]=4[O:54][CH2:53][CH2:52][N:51]3[CH:50]=2)=[N:47][CH:46]=[N:45]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131734228HCID 131734228, compound

Product 1

HCID 67050788HCID 67050788, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (179 mg, 0.47 mmol), ammonium chloride (50 mg, 0.942 mmol) and triethylamine (0.22 mL, 1.57 mmol) were added to a solution of (S)-2-{2-[2-(2,2,2-trifluoro-ethyl-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-ylamino}-propionic acid trifluoroacetate salt (168 mg, 0.314 mmol) in DMF (3 mL) and stirred for 18 hours. The reaction mixture was concentrated in vacuo and the residue treated with ethyl acetate and water, the organics layer separated, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 10% methanol in DCM), then trituration in water to give 529 (39 mg, 30%). LCMS: RT=3.23 min, [M+H]+=422. 1H NMR 400 MHz (DMSO-d6): δ 8.05 (1 H, s), 7.91 (1 H, s), 7.40 (1 H, br, s), 7.01 (1 H, br, s), 6.46 (1 H, dd, J=8.86, 2.33 Hz), 6.25 (1 H, d, J=7.11 Hz), 6.13 (1 H, d, J=2.29 Hz), 5.92 (2 H, q, J=8.89 Hz), 4.46-4.39 (4 H, m), 3.81 (1 H, t, J=6.96 Hz), 1.32 (3 H, d, J=6.87 Hz)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue treated with ethyl acetate and water
  3. customthe organics layer separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-162476d852494e4390240ff8a713c1b3
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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