Acetic Acid → HCID 135890150, compound

HRID 539870Notes

Reaction equation

HRID 539870 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.C(O)(=O)C.[O-:27][C:28]#[N:29].[K+]>O>[CH2:17]([C:10]1[N:9]=[C:8]([C:6]2[CH:7]=[C:2]([NH:1][C:28]([NH2:29])=[O: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 176Acetic AcidHCID 11378442Potassium cyanateHCID 136197415HCID 136197415, compound

Product 1

HCID 135890150HCID 135890150, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The compound (200 mg, 0.6 mmol) of example 42 was suspended in a mixed solution of water (5 ml) and acetic acid (5 ml), added with potassium cyanate (81 mg, 1 mmol), and heated to reflux and stirred for 2 h. The cooled reaction mixture was poured into water to generate a white solid, which was washed with water (10 ml×3) and dried to give the title compound (210 mg, yield: 91%). 1H NMR (DMSO-d6) δ: 11.76 (1H, br), 8.56 (1H, br), 7.76 (1H, d), 7.59 (1H, dd), 7.06 (1H, d), 5.78 (1H, br), 4.00 (2H, t), 2.56 (2H, q), 2.46 (2H, q), 1.74 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.97 (3H, t).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customThe cooled reaction mixture
  4. washwas washed with water (10 ml×3)
  5. customdried

Sources & evidence

ORD record
ord-4d89a2bb66a44d46a2d31ce29a001ec0
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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