Hydrochloric Acid → HCID 59556539, compound

HRID 1172974Notes

Reaction equation

HRID 1172974 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:32]=[CH:31][C:20]([CH2:21][NH:22][CH2:23][CH:24]4[CH2:28][O:27]C(C)(C)[O:25]4)=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:32]=[CH:31][C:20]([CH2:21][NH:22][CH2:23][CH:24]([OH:25])[CH2:28][OH:27])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59556608HCID 59556608, compound

Product 1

HCID 59556539HCID 59556539, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of N-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine (108 mg, 0.236 mmol) in THF (4 mL) was added 1N aqueous HCl (0.778 mL, 0.778 mmol) The reaction was heated to 65° C. under nitrogen for 90 minutes. Heating was stopped and the reaction was neutralized by addition of 1N aqueous NaOH (0.778 mL, 0.778 mmol). THF was removed under reduced pressure and the remaining aqueous solution was basified (pH approx 9) by the addition of 0.1N NaOH, at which point white precipitate formed. Solid was collected by vacuum filtration, and washed with 0.1N NaOH (3×10 mL). Solid was dried in a vacuum oven overnight to give 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzylamino)propane-1,2-diol (31.7 mg, 32%) as an off-white solid. LCMS (Table 1, Method c) Rt=1.90 min, m/z 418.47 (M+H)+; 1H NMR (400 MHz, methanol) δ ppm 7.22 (d, J=8.68 Hz, 1H), 7.60 (d, 2H), 8.01 (dd, 1H), 8.10 (d, 1H), 8.16 (d, 2H), 4.78 (sept, 1H), 2.76 (dd, 1H), 2.63 (dd, 1H), 3.52 (d, 2H), 3.90 (d, 2H), 3.78 (m, 1H), 1.40 (d, 6H).

Workup

  1. temperatureHeating
  2. customTHF was removed under reduced pressure
  3. additionby the addition of 0.1N NaOH
  4. customat which point white precipitate formed
  5. filtrationSolid was collected by vacuum filtration
  6. washwashed with 0.1N NaOH (3×10 mL)
  7. customSolid was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-2f2132d18c91472dbeff8bb14ddb408c
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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