Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 58394291, compound

HRID 2047590Notes

Reaction equation

HRID 2047590 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14](O)=[O:15])[C:11]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:10][N:9]=2)[CH:5]=[N:6][CH:7]=1.[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:32][NH2:33])=[N:28][C:29]=1[O:30][CH3:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:32][NH:33][C:14]([C:12]2[C:11]([N:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)=[CH:10][N:9]=[C:8]([C:4]3[CH:5]=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[CH:13]=2)=[O:15])=[N:28][C:29]=1[O:30][CH3:31]

Participants

5

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 574847121-(5,6-Dimethoxypyridin-2-yl)methanamineHCID 67333799HCID 67333799, compound

Product 1

HCID 58394291HCID 58394291, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5′-methyl-5-(1-pyrrolidinyl)-2,3′-bipyridine-4-carboxylic acid (2-2, 0.026 g, 0.085 mmol) and 1-(5,6-dimethoxy-2-pyridinyl)methanamine (3-6, 0.017 g, 0.102 mmol) in DMF (0.17 mL) was added HATU (0.032 g, 0.085 mmol) followed by DEA (0.074 mL, 0.426 mmol) and stirred at ambient temperature for 1 h. The system was partitioned between saturated aqueous sodium bicarbonate and EtOAc, washed with brine and dried over magnesium sulfate. Filtration and concentration followed by purification via normal phase chromatography (0→10% MeOH in EtOAc) afforded the title compound (2-3) as a salmon powder. 1H NMR (500 MHz, CDCl3) δ 8.93 (s, 1H), 8.40 (m, 1H), 8.32 (s, 1H), 8.06 (m, 1H), 7.08 (s, 1H), 7.06 (d, 1H, J=8.0 Hz), 6.90 (d, 1H, J=8.0 Hz), 4.63 (d, 2H, J=4.5 Hz), 4.00 (s, 3H), 3.89 (s, 3H), 3.36 (m, 4H), 2.40 (s, 3H), 1.93 (m, 4H). HRMS[M+H]C24H22N5O3 calc'd 434.2187. found 434.2211.

Workup

  1. customThe system was partitioned between saturated aqueous sodium bicarbonate and EtOAc
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration
  5. customfollowed by purification via normal phase chromatography (0→10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-bd94d1f69cf34ae28f3569948e6bccdd
Source dataset
uspto-grants-2013_11
Patent number
US08592457B2

Reaction notes

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