Water → HCID 178458514, compound

HRID 539872Notes

Reaction equation

HRID 539872 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][CH2:21][CH3:22])=[C:6]([C:8]2[NH:13][C:12](=[O:14])[C:11]([CH2:15][CH3:16])=[C:10]([CH2:17][CH3:18])[N:9]=2)[CH:7]=1.O.CS[C:26](=[NH:28])[NH2:27]>C(O)(=O)C>[CH2:17]([C:10]1[N:9]=[C:8]([C:6]2[CH:7]=[C:2]([NH:1][C:26]([NH2:28])=[NH:27])[CH:3]=[CH:4][C:5]=2[O:19][CH2:20][CH2:21][CH3:22])[NH:13][C:12](=[O:14])[C:11]=1[CH2:15][CH3:16])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 51422-Methyl-2-thiopseudoureaHCID 136197415HCID 136197415, compound

Product 1

HCID 178458514HCID 178458514, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound (140 mg, 0.41 mmol) of example 42 was suspended in a mixed solution of water (2.5 ml) and acetic acid (2.5 ml), added with S-methylisothiourea (64 mg, 0.45 mmol), and heated to reflux under stirring for 10 h. The reaction mixture was concentrated to dryness, dissolved in dichloromethane (20 ml), and washed orderly with 1N NaOH (5 ml), water (10 ml) and saturated saline. The organic phase was dried with anhydrous Na2SO4 and concentrated under reduced pressure to give an oil, which was passed through a silica gel column using ethyl acetate-petroleum ether as an eluant to obtain the title compound (35 mg, yield: 25%). 1H NMR (CDCl3) δ: 8.26 (1H, d), 8.00 (1H, dd), 7.50 (1H, br), 6.99 (1H, d), 4.14 (2H, t), 2.67 (2H, q), 2.59 (2H, q), 1.97 (2H, m), 1.29 (3H, t), 1.15 (3H, t), 1.13 (3H, t).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutiondissolved in dichloromethane (20 ml)
  5. washwashed orderly with 1N NaOH (5 ml), water (10 ml) and saturated saline
  6. dry with materialThe organic phase was dried with anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil, which

Sources & evidence

ORD record
ord-ab90ce4938ad47cd8c7155e526163413
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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