Triethylamine → HCID 53307541, compound

HRID 1497319Notes

Reaction equation

HRID 1497319 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([C:19]([NH:21][C@H:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]3[OH:28])=[O:20])[CH:10]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C>C(OCC)(=O)C.CO.[Pd]>[OH:28][C@H:23]1[CH2:24][CH2:25][CH2:26][CH2:27][C@@H:22]1[NH:21][C:19]([C:11]1[CH:10]=[C:9]([CH2:8][C:5]2[CH:6]=[N:7][CH:2]=[CH:3][CH:4]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)=[O:20]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 53307538HCID 53307538, compound

Product 1

HCID 53307541HCID 53307541, compound

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[(6-chloropyridin-3-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (A) (0.15 g, 0.38 mmol) in 3.5 mL ethyl acetate and a few drops of methanol to increase solubility was added triethylamine (0.053 mL, 0.38 mmol) and palladium on carbon (10 mol %). The reaction mixture was placed under a H2 (g) atmosphere with a balloon for 18 h. The reaction mixture was filtered through Celite, washed with excess methanol, and concentrated. The resulting residue was subjected to purification via reverse phase HPLC to afford the title compound that gave a mass ion (ES+) of 362.1866 for M+H+. 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 8.49 (dd, J=1.3, 4.8 Hz, 1H), 8.27 (d, J=7.7 Hz, 1H), 8.17 (s, 1H), 8.15 (dd J=0.7, 8.6 Hz, 1H), 8.01 (d, J=7.9 Hz, 1H), 7.78-7.74 (m, 1H), 7.63-7.52 (m, 1H), 7.44-7.42 (m, 1H), 7.19 (dd, J=4.9, 7.9 Hz, HA 4.51 (s, 2H), 3.93-3.84 (m, 1H), 3.62-3.54 (m, 1H), 3.36 (d, J=4.2, 1H), 2.17-2.12 (m, 2H) 1.82-1.79 (m, 2H), 1.52-1.34 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with excess methanol
  3. concentrationconcentrated
  4. customThe resulting residue was subjected to purification via reverse phase HPLC

Sources & evidence

ORD record
ord-0274d4d47ad04371baac25d4081b9b2e
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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