Toluene → {3-(3,4-Difluoro-phenyl)-3-[4-(1H-pyrazol-4-yl)-phenyl]-propyl}-methyl-amine

HRID 45493Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([CH:15]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:28]=[N:29][NH:30][CH:31]=3)=[CH:23][CH:22]=2)[CH2:16][C:17]([NH:19][CH3:20])=O)[CH:11]=[CH:12][C:13]=1[F:14].[Cl-].[Al+3].[Cl-].[Cl-].C1(C)C=CC=CC=1>C(OCC)C>[F:7][C:8]1[CH:9]=[C:10]([CH:15]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:31]=[N:30][NH:29][CH:28]=3)=[CH:23][CH:22]=2)[CH2:16][CH2:17][NH:19][CH3:20])[CH:11]=[CH:12][C:13]=1[F:14]

Participants

Conditions

Temperature: 70 °C

Procedure

Lithium aluminium hydride was added to a suspension of 3-(3,4-Difluoro-phenyl)-N-methyl-3-[4-(1H-pyrazol-4-yl)-phenyl]-propionamide in diethyl ether, followed by a solution of aluminium chloride in diethyl ether at 0° C., under a nitrogen atmosphere. Toluene was added and the reaction mixture was heated at 70° C. for 18 hours. Upon cooling the reaction was quenched with addition of water, basified (2N NaOH) and extracted with ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated to afford the desired compound. LC/MS: (PS-A2) Rt 2.15 [M+H]+ 328.06. 1H NMR (Me-d3-OD) δ 2.19-2.29 (2H, m), 2.35 (3H, s), 2.51 (2H, t), 4.00 (1H, t), 7.06-7.24 (3H, m), 7.27 (2H, d), 7.52 (2H, d), 7.92 (2H, s).

Workup

temperatureUpon cooling the reaction
customwas quenched with addition of water
extractionextracted with ethyl acetate
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-ffeee923824544f1ba773fdd21364aa5
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541461B2

Reaction notes

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