Trifluoroacetic acid → HCID 178501901, compound

HRID 1051694Notes

Reaction equation

HRID 1051694 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[NH:22][CH:23]=[C:24]([C:26]3[C:27]([O:41][CH:42]4[CH2:45][CH2:44][CH2:43]4)=[C:28]4[C:33](=[CH:34][CH:35]=3)[N:32]([C:36]([O:38][CH3:39])=[O:37])[C@@H:31]([CH3:40])[CH2:30][CH2:29]4)[N:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH:42]1([O:41][C:27]2[C:26]([C:24]3[N:25]=[C:21]([CH:18]4[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]4)[NH:22][CH:23]=3)=[CH:35][CH:34]=[C:33]3[C:28]=2[CH2:29][CH2:30][C@H:31]([CH3:40])[N:32]3[C:36]([O:38][CH3:39])=[O:37])[CH2:43][CH2:44][CH2:45]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178501902HCID 178501902, compound

Product 1

HCID 178501901HCID 178501901, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of (S)-methyl 6-(2-(1-(tert-butoxycarbonyl)piperidin-4-yl)-1H-imidazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.050 g, 0.09 mmol) in dichloromethane (6 mL), and the reaction mixture stirred at room temperature for 3 h. The reaction mixture was concentrated under vacuum, and the residue was purified via preparative-HPLC (Waters I): Column: Waters HSS C18, 2.1×50 mm, 1.8 um; Mobile Phase water (0.05% ammonium bicarbonate) and acetonitrile (5% to 95% acetonitrile in 10 min, flow rate: 20 mL/min); Detector: UV254&220 nm. This afforded methyl (S)-5-cyclobutoxy-2-methyl-6-(2-(piperidin-4-yl)-1H-imidazol-4-yl)-3,4-dihydroquinoline-1(2H)-carboxylate (0.0039 g, 10%) as an off-white solid. 1H NMR (300 MHz, CD3OD) δ ppm 1.15-1.26 (m, 2H), 1.32-1.68 (m, 3H), 1.95-2.55 (m, 8H), 2.97-3.19 (m, 3H), 3.40-3.47 (m, 2H), 3.77-3.82 (m, 2H), 4.13-4.25 (m, 1H), 4.51-4.71 (m, 3H), 7.28-7.47 (m, 2H), 8.55-8.61 (m, 1H). MS (ESI, pos. ion) m/z 425 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified via preparative-HPLC (Waters I)
  3. customMobile Phase water (0.05% ammonium bicarbonate) and acetonitrile (5% to 95% acetonitrile in 10 min, flow rate: 20 mL/min)

Sources & evidence

ORD record
ord-39eab0944e2347db9a40b7b33839459d
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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