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

HRID 1798342Notes

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-469c2ee7511b4c62bfaa82c253e09137
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343953B2

Reaction notes

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