Trifluoroacetic acid → HCID 58870664, compound

HRID 1927630Notes

Reaction equation

[CH2:1]([CH:3]([CH2:32][CH3:33])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19](O)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:15][CH2:14]2)=[C:9]([F:31])[CH:8]=1)=[O:5])[CH3:2].[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:32]([CH:3]([CH2:1][CH3:2])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([CH:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:15][CH2:14]2)=[C:9]([F:31])[CH:8]=1)=[O:5])[CH3:33]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-ethyl-N-{3-fluoro-4-[4-(1-hydroxy-1-phenyl-pentyl)-piperidin-1-yl]-phenyl}-butyramide (17 mg, 0.037 mmol) and Et3SiH (0.025 mL) in DCM (0.15 mL) was added TFA (0.25 mL). The mixture was stirred at 25° C. for 0.5 h and purified by PTLC to provide the title compound (9 mg, 55%). MS: 439.4. 1H NMR (CDCl3): 7.40 (dd, J=14.0, 2.5, 1H), 7.32-7.25 (m, 2H), 7.22-7.17 (m, 1H), 7.14-7.06 (m, 3H), 7.02 (s, 1H), 7.06 (t, J=9.2, 1H), 3.47-3.22 (m, 2H), 2.65-2.55 (m, 1H), 2.52-2.43 (m, 1H), 2.38-2.30 (m, 1H), 2.03 (m, 2H), 1.88-1.15 (m, 12H), 1.10-0.98 (m, 2H), 0.92 (t, J=7.4, 6H), 0.81 (t, J=7.3, 3H).

Workup

custompurified by PTLC

Sources & evidence

ORD record: ord-a0d70d3addb84cb4aff246ee81ed08fc
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183239B2

Reaction notes

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