Ammonium Chloride → HCID 58303896, compound

HRID 1404096Notes

Reaction equation

HRID 1404096 reaction equation
[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH3:12])[CH:6]=[C:5]2[CH:13]([CH3:17])[C:14](O)=[O:15].C[N:21](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-].CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH3:12])[CH:6]=[C:5]2[CH:13]([CH3:17])[C:14]([NH2:21])=[O:15]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58303983HCID 58303983, compound

Product 1

HCID 58303896HCID 58303896, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 9-3 (150 mg, 0.45 mmol), HATU (260 mg, 0.68 mmol) and NH4Cl (26 mg, 0.49 mmol) in THF (10 mL) was added DIPEA (147 mg, 0.57 mmol) at 0° C. The mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate (30 mL) and washed with brine twice. The combined organic layers were dried over anhydrous sodium sulfate. After filtration and concentration, the obtained residue was purified by flash chromatography (Silica gel, DCM:MeOH) to afford 9-4 (90 mg, 84%) as yellow oil.

Workup

  1. washwashed with brine twice
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationAfter filtration and concentration
  4. customthe obtained residue was purified by flash chromatography (Silica gel, DCM:MeOH)

Sources & evidence

ORD record
ord-870e2ba17c8d4d17a621f2d2e349ce91
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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