2,2,2-Trifluoroethanol → HCID 57550039, compound

HRID 1518441Notes

Reaction equation

HRID 1518441 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26]C(C)(C)C)=O)[CH2:20][CH2:19]3)=[CH:13][C:12]2=[O:31])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:32][C:33]([F:37])([F:36])[CH2:34][OH:35].F[C:39](F)(F)[CH:40](O)C>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]3[CH2:19][C@@H:20]4[N:21]([C:24]([O:35][CH2:34][C:33]([F:37])([F:36])[F:32])=[O:26])[C@H:22]([CH2:39][CH2:40]4)[CH2:23]3)=[CH:13][C:12]2=[O:31])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 97741,1,1-Trifluoro-2-propanolHCID 25204174Tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 57550039HCID 57550039, compound

Procedure

Example 112 was prepared according to procedures described in Example 2 substituting (3-exo)-tert-butyl 3-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (Example 25) for tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate at Step A and 2,2,2-trifluoroethanol for 1,1,1-trifluoro-2-propanol at Step B. 1H NMR (500 MHz, CDCl3) δ 8.08 (d, J=8.80 Hz, 2 H), 7.61 (d, J=8.80 Hz, 2 H), 7.20-7.32 (m, 1 H), 6.24 (d, J=2.75 Hz, 1 H), 6.09 (dd, J=7.70, 2.75 Hz, 1 H), 4.73-4.87 (m, 1 H), 4.54-4.67 (m, 1 H), 4.39-4.55 (m, 3 H), 3.10 (s, 3 H), 2.17-2.30 (m, 2 H), 2.04-2.19 (m, 2H), 1.68-1.94 (m, 4 H). MS (ESI) 501 (M+H).

Workup

  1. customExample 112 was prepared

Sources & evidence

ORD record
ord-c35d922079334920977b7c6d65c8e71a
Source dataset
uspto-grants-2012_07
Patent number
US08232404B2

Reaction notes

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