Ammonium Chloride → HCID 66589143, compound

HRID 1092228Notes

Reaction equation

HRID 1092228 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:17]([N+:18]([O-])=O)=[CH:16][C:13]([C:14]#[N:15])=[C:12]([NH:21][C@H:22]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[CH3:23])[CH:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[Cl-].[NH4+].C([O-])(=O)C.[NH4+]>CO.C1COCC1.[Zn]>[NH2:18][C:17]1[C:10]([NH:9][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:8][N:7]=2)=[CH:11][C:12]([NH:21][C@H:22]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH3:23])=[C:13]([CH:16]=1)[C:14]#[N:15]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 517165Ammonium AcetateHCID 11596606HCID 11596606, compound

Product 1

HCID 66589143HCID 66589143, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of (S)-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-[1-(4-fluorophenyl)ethylamino]-5-nitrobenzonitrile (Method 32; 4.10 g, 10.1 mmol) and zinc dust (3.30 g, 50.4 mmol) in MeOH:THF (1:1, 100 ml) was slowly added saturated ammonium chloride (40 ml). The reaction mixture was stirred at 25° C. for 1 hr, to which was added saturated ammonium acetate solution (50 ml). The resulting mixture was stirred for another 30 min. The Zn dust was removed by filtration and washed with EtOAc (200 ml). The organic layer was separated, washed with brine (100 ml), dried over Na2SO4, and concentrated. The title compound was used directly for the next step without further purification. MS: Calcd: 376; Found: [M+H]+ 377.

Workup

  1. stirringThe resulting mixture was stirred for another 30 min
  2. customThe Zn dust was removed by filtration
  3. washwashed with EtOAc (200 ml)
  4. customThe organic layer was separated
  5. washwashed with brine (100 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe title compound was used directly for the next step without further purification

Sources & evidence

ORD record
ord-625b2d080cfc4bd2a654ec8f6e994478
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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