Trifluoroacetic acid → HCID 25261412, compound

HRID 268807Notes

Reaction equation

C(O[C:6](=O)[N:7]([CH2:9][CH2:10][CH:11]([C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:22]=[CH:21]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C)(C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:30][S:27]([N:23]1[C:24]2[C:20](=[CH:19][C:18]([CH:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:10][CH2:9][NH:7][CH3:6])=[CH:26][CH:25]=2)[CH:21]=[CH:22]1)(=[O:29])=[O:28]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of [3-(1-Methanesulfonyl-1H-indol-5-yl)-3-phenyl-propyl]-methyl-carbamic acid tert-butyl ester LXXVI (56 mg, 0.127 mmol) in DCM (3 ml) was added triethylsilane (300 μl) and TFA (1.5 ml). The resulting mixture was stirred at 0° C. for 5 minutes and at room temperature for 40 minutes. The mixture was concentrated, and the residue was partitioned between a saturated solution of NaHCO3 and EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH/NH4OH) affording [3-(1-Methanesulfonyl-1H-indol-5-yl)-3-phenyl-propyl]-methyl-amine LXXVIII as a white solid (31 mg, 71% yield). The amine LXXVIII (31 mg, 71% yield) was dissolved in Et2O (3 ml) and HCl (1M in Et2O, 95 μl) was added. The precipitate was filtered, washed with Et2O and dried in vacuo to afford the hydrochloride as a white powder (33 mg, 96% yield). MS (M+H)=343

Workup

concentrationThe mixture was concentrated
customthe residue was partitioned between a saturated solution of NaHCO3 and EtOAc
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record: ord-a50882b465bd4cd3869d61780210b12d
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446118B2

Reaction notes

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