HCID 58625824, compound → HCID 11512463, compound

HRID 2116899Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[NH:25][C:26]([C:37]4[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=4)=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=4)[N:28]=3)[C@H:20]([CH3:47])[CH2:19]2)=[N:4][CH:5]=[C:6]([CH2:8][O:9]COCC[Si](C)(C)C)[CH:7]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[N:4][C:3]=1[N:18]1[CH2:23][CH2:22][N:21]([C:24]2[NH:25][C:26]([C:37]3[CH:38]=[CH:39][C:40]([C:43]([F:46])([F:44])[F:45])=[CH:41][CH:42]=3)=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=3)[N:28]=2)[C@H:20]([CH3:47])[CH2:19]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (2R)-4-(3-chloro-5-(((2-(trimethylsilyl)ethoxy)methoxy)methyl)pyridin-2-yl)-1-(4-(3,4-difluorophenyl)-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)-2-methylpiperazine from step (b) above (160 mg, 0.23 mmol) in TFA (3 mL) was stirred at RT for 1.5 h. The solvent was removed and the residue was added solution of MeOH:DCM (1:1, 3 mL). The mixture was cooled to 0° C. and potassium carbonate (200 mg) was added. The mixture was then stirred at RT for 2.5 h and the solvents were removed. The residue was purified on silica gel using ISCO Combiflash® system with EtOAc/Hexanes (1:1) as the eluant to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 564 (M+1).

Workup

customThe solvent was removed
additionthe residue was added solution of MeOH:DCM (1:1, 3 mL)
additionpotassium carbonate (200 mg) was added
customthe solvents were removed
customThe residue was purified on silica gel using ISCO Combiflash® system with EtOAc/Hexanes (1:1) as the eluant

Sources & evidence

ORD record: ord-8e9385ce0f4e485b8e8524d817aa622a
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439360B2

Reaction notes

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