Hydrochloric Acid → HCID 178445800, compound

HRID 525440Notes

Reaction equation

HRID 525440 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([C:29]([O:31]C)=[O:30])[CH2:25][CH2:24]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.Cl>CO>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([C:29]([OH:31])=[O:30])[CH2:27][CH2:28]2)[CH:16]=[CH:15]3)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178498392HCID 178498392, compound

Product 1

HCID 178445800HCID 178445800, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 1-((6-(trans-4-tert-butylcyclohexyloxy)quinolin-2-yl)methyl)piperidine-4-carboxylate (150 mg, 0.34 mmol) in MeOH (5 mL) was added NaOH (68 mg, 1.7 mmol, 5.0 eq) and H2O (0.5 mL). The reaction mixture was stirred at 85° C. for 2 h. Then the reaction was cooled to 0° C., the pH of the solution was adjusted to 6 with 3 N HCl. The mixture was filtrated, and the yellow solid was the desired product 1-((6-(trans-4-tert-butylcyclohexyloxy)quinolin-2-yl)methyl)piperidine-4-carboxylic acid (90 mg, yield: 46%). ESI-MS (M+1)+: 425.3, HPLC: 100%. 1H NMR (400 MHz, DMSO-d6) δ: 8.32 (d, 1H), 7.93 (d, 1H), 7.70 (d, 1H), 7.48 (s, 1H), 7.41 (d, 1H), 4.53 (br, 1H), 4.44˜4.40 (m, 1H), 3.33 (br, 3H), 3.14 (br, 2H), 2.49 (br, 1H), 2.22˜2.20 (m, 2H), 2.04˜1.80 (m, 6H), 1.37˜1.32 (m, 2H), 1.25˜1.20 (m, 2H), 1.10˜1.08 (m, 1H), 0.87 (s, 9H).

Workup

  1. temperatureThen the reaction was cooled to 0° C.
  2. filtrationThe mixture was filtrated

Sources & evidence

ORD record
ord-1eeda41fe9c14c54a9e96ab7b8696115
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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