Sodium Bicarbonate → HCID 59451452, compound

HRID 1874847Notes

Reaction equation

HRID 1874847 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([O:34][C:35]2[C:40]([Cl:41])=[CH:39][CH:38]=[C:37]([CH2:42][NH:43][CH3:44])[C:36]=2[F:45])[CH:33]=1)[C:29]#[N:30].[NH:46]1[CH:50]=[CH:49][N:48]=[C:47]1[C:51]([OH:53])=O.C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:41][C:40]1[CH:39]=[CH:38][C:37]([CH2:42][N:43]([CH3:44])[C:51]([C:47]2[NH:46][CH:50]=[CH:49][N:48]=2)=[O:53])=[C:36]([F:45])[C:35]=1[O:34][C:32]1[CH:31]=[C:28]([C:29]#[N:30])[CH:27]=[C:26]([Cl:25])[CH:33]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5743211H-Imidazole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59451460HCID 59451460, compound

Product 1

HCID 59451452HCID 59451452, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (0.16 g, 0.43 mmol) was added to a solution of 3-chloro-5-({6-chloro-2-fluoro-3-[(methylamino)methyl]phenyl}oxy)benzonitrile (0.10 g, 0.30 mmol) and 1H-imidazole-2-carboxylic acid (0.05 g, 0.43 mmol) in DMF (3 mL) and the solution was stirred at RT overnight. After 16 h, ethyl acetate (100 ml) and saturated NaHCO3 solution (100 ml) were added. The organic layer was separated, washed with saturated NaHCO3 solution (2×100 ml), brine (150 mL), dried over MgSO4, filtered and concentrated. The crude material was purified by Reverse Phase HPLC to give the title compound (0.025 g, 20%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.82 (s, 1H), 7.46-7.57 (m, 3H), 7.27-7.37 (m, 2H), 7.18 (s, 1H), 5.57 (s, 1H), 4.77 (s, 1H), 3.53 (s, 1.5H), 2.98 (s, 1.5H). 19F NMR (376 MHz, DMSO-d6) δ ppm −75.19 (s, 1F). LCMS m/z 418 (M−1).

Workup

  1. waitAfter 16 h
  2. customThe organic layer was separated
  3. washwashed with saturated NaHCO3 solution (2×100 ml), brine (150 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by Reverse Phase HPLC

Sources & evidence

ORD record
ord-b58a9d8151ce43df945704fc9a17bc58
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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