Ammonia → HCID 86270996, compound

HRID 2170210Notes

Reaction equation

HRID 2170210 reaction equation
[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[NH:16][C:17]([CH3:28])=[C:18]2[C:23]=1[CH:22]=[C:21]([C:24](O)=[O:25])[NH:20][C:19]2=[O:27].C[N:35](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.N>CN(C)C=O>[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:12])=[O:13])=[CH:7][C:6]=1[C:15]1[NH:16][C:17]([CH3:28])=[C:18]2[C:23]=1[CH:22]=[C:21]([C:24]([NH2:35])=[O:25])[NH:20][C:19]2=[O:27]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86270903HCID 86270903, compound

Product 1

HCID 86270996HCID 86270996, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 40 (0.05 g, 0.105 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.048 g, 0.126 mmol), N-ethyl-N-isopropylpropan-2-amine (0.092 mL, 0.527 mmol) and 0.5 M ammonia (1.054 mL, 0.527 mmol) in dimethylformamide (1 mL) was stirred at ambient temperature for 4 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated. Purification by reverse phase chromatography (C18, CH3CN/10 mM ammonium acetate in water, 10-100% gradient) afforded the title compound (0.011 mg, 22%). 1H NMR (300 MHz, DMSO-d6) δ 8.96-9.08 (m, 1H), 8.00 (d, J=2.37 Hz, 1H), 7.96-7.99 (m, 1H), 7.82 (dd, J=8.48, 2.37 Hz, 1H), 7.44-7.63 (m, 3H), 7.28 (s, 1H), 7.18-7.27 (m, 1H), 6.99 (d, J=7.46 Hz, 1H), 3.26 (s, 3H), 2.67 (s, 3H). MS (ESI+) m/z 474 [M+H]+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried (anhydrous sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by reverse phase chromatography (C18, CH3CN/10 mM ammonium acetate in water, 10-100% gradient)

Sources & evidence

ORD record
ord-dd05d2b69aa443d78745b7a50447ed8b
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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