Ammonium Chloride → HCID 67478851, compound

HRID 1092227Notes

Reaction equation

HRID 1092227 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:11]=[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])[CH:13]=[CH:14][C:15]=3[N+:16]([O-])=O)[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:19][C@H:20]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[CH3:21])[CH:13]=[CH:14][C:15]=3[NH2:16])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 517165Ammonium AcetateHCID 67478765HCID 67478765, compound

Product 1

HCID 67478851HCID 67478851, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of (S)-N3-(5-cyclopropyl-1H-pyrazol-3-yl)-N1-[1-(4-fluorophenyl)ethyl]-4-nitrobenzene-1,3-diamine (Method 26; 0.37 g, 0.97 mmol) and Zinc dust (0.317 g, 4.85 mmol) in MeOH:THF (1:1, 24 ml) was slowly added saturated ammonium chloride (3.0 ml). The reaction mixture was stirred at 25° C. for 1 hr, to which was then added saturated ammonium acetate solution (5 ml). The resulting mixture was stirred for another 30 min. 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. The crude product was used directly for the next step without further purification. MS: Calcd: 351; Found: [M+H]+ 352.

Workup

  1. stirringThe resulting mixture was stirred for another 30 min
  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
  8. customThe crude product was used directly for the next step without further purification

Sources & evidence

ORD record
ord-c449fee717194a579a1c41f35d6dac54
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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