Ammonium Chloride → HCID 67478794, compound

HRID 1092216Notes

Reaction equation

HRID 1092216 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][N: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.[NH4+].[Cl-]>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][N: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

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67478923HCID 67478923, compound

Product 1

HCID 67478794HCID 67478794, compoundYield 5.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a suspension of (S)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-[1-(4-fluorophenyl)ethyl]-5-nitropyrimidine-2,4-diamine (Method 9; 0.8 g, 2.0 mmol) and zinc dust (0.7 g, 10.0 mmol) in MeOH:THF (1:1, 50 ml) was slowly added saturated NH4Cl solution (10 ml) at 25° C. After 3 hours, the reaction mixture was treated with saturated aqueous NH4OAc solution (40 ml) and allowed to stir for 30 minutes. The reaction was then filtered through a plug of celite with EtOAc (100 ml), and the resulting aqueous layer was extracted with EtOAc (2×100 ml), dried, filtered, and concentrated to give the title compound (0.04 g, 5%). MS: Calcd.: 353; Found: [M+H]+ 354.

Workup

  1. customat 25° C
  2. filtrationThe reaction was then filtered through a plug of celite with EtOAc (100 ml)
  3. extractionthe resulting aqueous layer was extracted with EtOAc (2×100 ml)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6a47635589de49faabcbb1009e643cb5
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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