Hydrochloric Acid → HCID 118566573, compound

HRID 1056802Notes

Reaction equation

HRID 1056802 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:36])[C:20]=3[C:24](=[O:35])[NH:25][CH2:26][CH:27]3[CH2:32][CH2:31][C:30]([F:34])([F:33])[CH2:29][CH2:28]3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCl.Cl.O1CCOCC1.C(=O)(O)[O-].[Na+]>>[F:34][C:30]1([F:33])[CH2:31][CH2:32][CH:27]([CH2:26][NH:25][C:24]([C:20]2[C:21]3[CH:22]=[CH:23][C:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[N:15][C:16]=3[CH:17]=[CH:18][C:19]=2[Cl:36])=[O:35])[CH2:28][CH2:29]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 118555958HCID 118555958, compound

Product 1

HCID 118566573HCID 118566573, compoundYield 24.5%

Procedure

To a stirred solution of 4-{6-chloro-5-[(4,4-difluoro-cyclohexylmethyl)-carbamoyl]-quinolin-2-yl}-piperidine-1-carboxylic acid tert-butyl ester (50 mg, 0.09 mmol, 1.00 eq) in dichloromethane (5.00 mL, 77.14 mmol, 100 V) at 0 OC was added 4M HCl in dioxane (2 mL, 8.00 mmol, 89.05 eq) dropwise under nitrogen. The reaction mixture was stirred at RT for 2 h and the solvent was evaporated completely. The crude obtained was basified with 10% sodium bicarbonate solution and was extracted with DCM. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The crude obtained was purified by preparative HPLC to afford the title compound (10 mg, 0.02 mmol, 24.5%) as a pale brown solid. 1H NMR (400 MHz, DMSO-d6): δ 8.79 (t, J=5.91 Hz, 1H), 7.99 (dd, J=9.42, 9.0 Hz, 2H), 7.76 (d, J=9.03 Hz, 1H), 7.58 (d, J=8.72 Hz, 1H), 3.43 (s, 1H), 3.25-3.29 (m, 2H), 3.03-3.06 (m, 2H), 2.91-2.98 (m, 1H), 2.58-2.67 (m, 2H), 2.02-2.04 (m, 2H), 1.64-1.84 (m, 9H), 1.23-1.30 (m, 2H). m/z: 422.0 [M+H]+

Workup

  1. customthe solvent was evaporated completely
  2. customThe crude obtained
  3. extractionwas extracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude obtained
  8. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-6a7bb80766304d7cae8a35f64e09efb1
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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