Water → 3-[(2(S)-Azetidinyl)methoxy]-5-[4-[2-(benzyloxy)ethyl]phenyl]pyridine Trifluoroacetate

HRID 2095340Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].O.[CH2:9]([O:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[N:27][CH:28]=[C:29]([O:31][CH2:32][C@@H:33]3[CH2:36][CH2:35][N:34]3C(OC(C)(C)C)=O)[CH:30]=2)=[CH:21][CH:20]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH:34]1[CH2:35][CH2:36][C@H:33]1[CH2:32][O:31][C:29]1[CH:28]=[N:27][CH:26]=[C:25]([C:22]2[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][O:16][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:20][CH:21]=2)[CH:30]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Trifluoroacetic acid (1.0 mL) and water (0.11 mL) were added to CH2Cl2 (5.5 mL). This mixture was added to 3-[4-[2-(benzyloxy)ethyl]phenyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]pyridine (220 mg, 0.46 mmol) in a 25 mL round-bottom flask with a magnetic stirrer under N2. After stirring at 30° C. for 24 h, TLC analysis indicated that the starting material had disappeared. The reaction mixture was concentrated, and the residue was purified by preparative HPLC (SunFire Prep C18 column, 19×150 mm, 5 μm particle size; UV detection at 254 nm; flow 15 mL/min; CH3CN/water gradient with addition of 0.05% CF3COOH, from 20-40% CH3CN in 6 min) to provide the title compound (140 mg, light-yellow solid) as a partial trifluoroacetate.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by preparative HPLC (SunFire Prep C18 column, 19×150 mm, 5 μm particle size; UV detection at 254 nm; flow 15 mL/min; CH3CN/water gradient with addition of 0.05% CF3COOH, from 20-40% CH3CN in 6 min)

Sources & evidence

ORD record: ord-112d93d38f2a45f88a4aeb71eec5d4ea
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445684B2

Reaction notes

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