Hydrochloric Acid → HCID 53966964, compound

HRID 1919295Notes

Reaction equation

HRID 1919295 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-6e6afe6edd304b3ab8215c511e8f9b63
Source dataset
uspto-grants-2012_05
Patent number
US08168627B2

Reaction notes

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