Ammonium Chloride → (S)-N3-(5-Cyclopropyl-1H-pyrazol-3-yl)-2-fluoro-N1-[1-(4-fluorophenyl)ethyl]benzene-1,3,4-triamine

HRID 1092229Notes

Reaction equation

[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:11]([F:29])=[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[C:11]([F:29])=[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

Conditions

Temperature: 25 °C

Procedure

To a suspension of (S)-N3-(5-cyclopropyl-1H-pyrazol-3-yl)-2-fluoro-N1-[1-(4-fluorophenyl)ethyl]-4-nitrobenzene-1,3-diamine (Method 36; 0.40 g, 1.00 mmol) and zinc dust (0.327 g, 5.00 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 hours, to which was then added saturated ammonium acetate solution (5 ml). The resulting mixture was stirred for another 30 minutes. The Zn dust was removed by filtration and washed with EtOAc (15 ml). The organic layer was separated, washed with brine, dried over Na2SO4, and concentrated. The title compound was used directly for the next step without further purification.

Workup

stirringThe resulting mixture was stirred for another 30 minutes
customThe Zn dust was removed by filtration
washwashed with EtOAc (15 ml)
customThe organic layer was separated
washwashed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe title compound was used directly for the next step without further purification

Sources & evidence

ORD record: ord-b0d998a036f143fd98d404479dbba517
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129403B2

Reaction notes

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