Ammonia → HCID 86270803, compound

HRID 2170206Notes

Reaction equation

HRID 2170206 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])=[C:6]([C:8]2[NH:9][C:10]([CH3:21])=[C:11]3[C:16]=2[CH:15]=[C:14]([C:17]([OH:19])=O)[NH:13][C:12]3=[O:20])[CH:7]=1.C[N:32](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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])=[C:6]([C:8]2[NH:9][C:10]([CH3:21])=[C:11]3[C:16]=2[CH:15]=[C:14]([C:17]([NH2:32])=[O:19])[NH:13][C:12]3=[O:20])[CH:7]=1

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 90386774HCID 90386774, compound

Product 1

HCID 86270803HCID 86270803, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 32a (0.07 g, 0.162 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.074 g, 0.195 mmol), N-ethyl-N-isopropylpropan-2-amine (0.142 mL, 0.812 mmol) and 0.5 M ammonia (1.625 mL, 0.812 mmol) in dimethylformamide (1 mL) was stirred at ambient temperature for two 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 (0.022 mg, 31%). 1H NMR (400 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.95 (s, 1H), 8.07 (s, 1H), 7.56 (d, J=2.44 Hz, 1H), 7.40-7.52 (m, 2H), 7.26-7.39 (m, 3H), 7.06-7.15 (m, 1H), 6.87 (d, J=8.85 Hz, 1H), 2.63 (s, 3H). MS (APCI+) m/z 430 [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-ea0ceb661aff42e68590554348a05e67
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

Loading…