Ammonium Chloride → HCID 67478890, compound

HRID 1092230Notes

Reaction equation

HRID 1092230 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][C:13]([F:19])=[C:12]([NH:20][C@H:21]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH3:22])[CH: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[CH:11]=[C:12]([NH:20][C@H:21]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)[CH3:22])[C:13]([F:19])=[CH:14][C:15]=3[NH2:16])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 517165Ammonium AcetateHCID 11502190HCID 11502190, compound

Product 1

HCID 67478890HCID 67478890, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of (S)-N1-(5-cyclopropyl-1H-pyrazol-3-yl)-4-fluoro-N3-[1-(4-fluorophenyl)ethyl]-6-nitrobenzene-1,3-diamine (Method 38; 0.33 g, 0.826 mmol) and Zinc dust (0.270 g, 4.13 mmol) in MeOH:THF (1:1, 10 ml) was slowly added saturated ammonium chloride (4 ml). The mixture was stirred at 25° C. for 2 hrs, to which was added saturated ammonium acetate solution (5 ml). The resulting mixture was stirred for another 30 min. The Zn dust was removed by filtration and washed with EtOAc (15 ml). The organic layer was separated and dried over Na2SO4. After removal of solvent, the title compound was used directly for the next step without further purification.

Workup

  1. stirringThe resulting mixture was stirred for another 30 min
  2. customThe Zn dust was removed by filtration
  3. washwashed with EtOAc (15 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customAfter removal of solvent
  7. customthe title compound was used directly for the next step without further purification

Sources & evidence

ORD record
ord-ad605449eab24bc9af7909745d476169
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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