Hydrochloric Acid → HCID 53966964, compound

HRID 2233598Notes

Reaction equation

HRID 2233598 reaction equation
[CH3:1][C:2]1([CH3:25])[C:6](=N)[N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[C:4](=[S:20])[N:3]1[CH2:21][CH2:22][CH2:23][OH:24].Cl.C[OH:28]>>[CH3:1][C:2]1([CH3:25])[C:6](=[O:28])[N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:18])([F:19])[F:17])[CH:9]=2)[C:4](=[S:20])[N:3]1[CH2:21][CH2:22][CH2:23][OH:24]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 22116936HCID 22116936, compound

Product 1

HCID 53966964HCID 53966964, compoundYield 68%

Procedure

To a solution of compound 4a (627 mg, 1.7 mmol) in methanol (27 mL) was added 2N aqueous hydrogen chloride (5.2 mL). The solution was refluxed for 90 min and then poured in an ice/water solution. The solution was extracted with ethyl acetate (3×30 mL), washed with brine, and dried over magnesium sulphate to give 428 mg (68%) of desired compound 5a. 1H NMR (400 MHz, Acetone-d6) δ: 1.65 (s, 6H), 3.67 (q, 2H, J=5.7 Hz), 3.75 (t, 1H, J=5.01 Hz), 3.90 (m, 2H), 8.03 (d, 1H, J=6.4 Hz), 8.18 (s, 1H), 8.26 (d, 1H, J=8.26 Hz).

Workup

  1. temperatureThe solution was refluxed for 90 min
  2. extractionThe solution was extracted with ethyl acetate (3×30 mL)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-703a05d39bda4c7db5f2e6c9b8095b06
Source dataset
uspto-grants-2010_05
Patent number
US07709516B2

Reaction notes

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