Triethylamine → (3S)-N-{1-[(3-Fluoro-5-phenyl-1-benzothiophen-2-yl)carbonyl]azetidin-3-yl}-1-(phenylcarbonyl)pyrrolidin-3-amine

HRID 403297Notes

Reaction equation

[NH:1]1[CH2:4][CH:3]([NH:5][C@H:6]2[CH2:10][CH2:9][N:8]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[CH2:7]2)[CH2:2]1.CCN(CC)CC.[F:26][C:27]1[C:28]2[CH:38]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:36]=[CH:35][C:29]=2[S:30][C:31]=1[C:32](Cl)=[O:33]>C(Cl)Cl>[F:26][C:27]1[C:28]2[CH:38]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:36]=[CH:35][C:29]=2[S:30][C:31]=1[C:32]([N:1]1[CH2:2][CH:3]([NH:5][C@H:6]2[CH2:10][CH2:9][N:8]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[CH2:7]2)[CH2:4]1)=[O:33]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of compound 5e (42.7 mg, 0.131 mmol) and Et3N (0.07 mL, 0.5 mmol) in CH2Cl2 (2 mL) at 0° C. was slowly added a solution of compound 13e (36.3 mg, 0.125 mmol) in CH2Cl2 (1 mL). The reaction was stirred at 0° C. for 2 h, diluted with CH2Cl2, and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography (silica gel, % MeOH/EtOAc) to give compound Cpd 173 (16.7 mg). MS m/z (M+H+) 500.

Workup

washwashed with aqueous NaHCO3
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
customThe residue was purified by flash column chromatography (silica gel, % MeOH/EtOAc)

Sources & evidence

ORD record: ord-075520bfffc343d8afc855488f3ab042
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748417B2

Reaction notes

Loading…