Ammonium Chloride → HCID 67478925, compound

HRID 75884Notes

Reaction equation

HRID 75884 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[C:12]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH3:21])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[Cl-].[NH4+].C([O-])(=O)C.[NH4+]>CO.C1COCC1.[Zn]>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([NH:19][C@H:20]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[CH3:21])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 517165Ammonium AcetateHCID 11516485HCID 11516485, compound

Product 1

HCID 67478925HCID 67478925, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of (S)—N2-(5-cyclopropyl-1H-pyrazol-3-yl)-N6-[1-(4-fluorophenyl)ethyl]-3-nitropyridine-2,6-diamine (Example 47; 0.26 g, 0.68 mmol) and zinc dust (0.223 g, 3.41 mmol) in MeOH:THF (1:1, 12 ml) was slowly added saturated ammonium chloride solution (1.5 ml). The reaction mixture was stirred at 25° C. for 1 hour, to which was then added saturated ammonium acetate solution (5 ml). The resulting mixture was stirred for another 30 minutes. Zn dust was removed by filtration and washed with EtOAc (20 ml). The organic layer was separated, washed with brine (10 ml), dried over Na2SO4, and concentrated to give the title compound.

Workup

  1. stirringThe resulting mixture was stirred for another 30 minutes
  2. customZn dust was removed by filtration
  3. washwashed with EtOAc (20 ml)
  4. customThe organic layer was separated
  5. washwashed with brine (10 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3f5c57ff7b2048fcb8e79b569d9b6806
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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