Hydrochloric Acid → HCID 70873687, compound

HRID 2208853Notes

Reaction equation

HRID 2208853 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH2:21][CH3:22])[CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH2:21][CH3:22])[CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70873808HCID 70873808, compound

Product 1

HCID 70873687HCID 70873687, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 5-chloro-3-[ethyl(oxan-4-yl)amino]-2-methoxybenzoate (127 mg, 0.39 mmol) in THF (4 ml) was added 4M NaOH (3.87 ml). The reaction mixture was stirred at 50° C. for 24 hours. The reaction mixture was acidified to pH 2-3 with 6M HCl and extracted with DCM (5×15 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give 111 mg (91%) of the title compound as a yellow oil. LC-MS 80%, 1.25 min (3 minute LC-MS method), m/z=314.4/315.9, 1H NMR (500 MHz, Chloroform-d) δ ppm 10.02-9.55 (m, 1H), 8.01-7.47 (m, 1H), 7.36-6.96 (m, 1H), 4.15-3.86 (m, 5H), 3.76 (t, J=6.6 Hz, 2H), 3.55-3.12 (m, 3H), 1.95-1.59 (m, 4H), 1.15-0.88 (m, 3H).

Workup

  1. extractionextracted with DCM (5×15 ml)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ad6e91e9d924e3f90817b34078cd933
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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