Ammonium Chloride → HCID 178489996, compound

HRID 1627307Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:34]([F:35])=[CH:33][C:28]([O:29][CH2:30][C:31]#[N:32])=[CH:27][C:26]=3[F:36])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:37][CH3:38].[NH4+].[Cl-].[N-:41]=[N+:42]=[N-:43].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:26]([F:36])=[CH:27][C:28]([O:29][CH2:30][C:31]4[NH:43][N:42]=[N:41][N:32]=4)=[CH:33][C:34]=3[F:35])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:37][CH3:38]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)acetonitrile (129 mg, 0.23 mmol), NH4Cl (124 mg, 2.3 mmol) and NaN3 (16.60 mg, 0.25 mmol) in DMF (1.5 mL) was heated 17 h at 90° C. The reaction mixture was partitioned in EtOAc and H2O. The organic layer was washed with H2O and brine, dried over Na2SO4 and purified by flash chromatography (20% MeOH/DCM) to give the title compound (93 mg, 67%). 1HNMR (400 MHz, DMSO-d6) δ7.23 (d, J=8.3 Hz, 1H), 7.18 (s, 1H), 6.96 (m, 2H), 6.82 (m, 2H), 6.57-6.45 (m, 4H), 5.30 (s, 2H), 3.95 (s, 2H), 3.68 (s, 3H), 1.46 (s, 6H); MS (EI) m/z 601.3 (MH+).

Workup

customThe reaction mixture was partitioned in EtOAc
washThe organic layer was washed with H2O and brine
dry with materialdried over Na2SO4
custompurified by flash chromatography (20% MeOH/DCM)

Sources & evidence

ORD record: ord-8d41804c9eb04a9aa5485a49a9c52508
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785488B2

Reaction notes

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