Potassium Hydroxide → HCID 9846074, compound

HRID 1274137Notes

Reaction equation

HRID 1274137 reaction equation
[OH-].[K+].C[O:4][C:5]([C:7]1[C:12]([NH2:13])=[N:11][C:10]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[N:30]=[C:29]([NH2:31])[C:28]4[C:23](=[CH:24][C:25]([O:34][CH3:35])=[C:26]([O:32][CH3:33])[CH:27]=4)[N:22]=3)[CH2:17][CH2:16]2)=[CH:9][N:8]=1)=[O:6]>CO.O>[NH2:13][C:12]1[C:7]([C:5]([OH:6])=[O:4])=[N:8][CH:9]=[C:10]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[N:30]=[C:29]([NH2:31])[C:28]4[C:23](=[CH:24][C:25]([O:34][CH3:35])=[C:26]([O:32][CH3:33])[CH:27]=4)[N:22]=3)[CH2:17][CH2:16]2)[N:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 9933665HCID 9933665, compound

Product 1

HCID 9846074HCID 9846074, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
85 °C

Procedure

Potassium hydroxide (0.53 g, 9.46 mmol) was added to a solution of (2) (0.23 g, 0.47 mmol) in MeOH/H2O (20 mL, 10%; v/v) at 25° C. The reaction mixture was heated at 85° C. for 12 h then cooled to room temperature. The mixture was concentrated, acidified with HCl (aq) (20 mL, 3M) and the desired product was filtered and rinsed with cold H2O to give 0.21 g (93%) of the title compound: 1H NMR (DMSO) δ 12.45 (br s, 1H), 8.78 (br, 2H), 8.37 (s, 1H), 7.78 (s, 1H), 7.68 (s, 1H), 7.38 (s, 1H), 5.19 (br s, 3H), 4.56 (m, 2H), 4.13 (m, 1H), 3.85 (s, 3H), 3.83 (s, 3H), 3.41 (m, 2H), 2.04 (m, 2H), 1.54 (m, 2H); 13C NMR (DMSO) δ 167.0, 161.3, 155.8, 155.1, 154.4, 151.0, 146.7, 136.3, 121.3, 121.0, 105.2, 101.6, 99.3, 56.3, 56.0, 46.5, 43.3, 30.5; HRMS (FAB) m/z 441.1988 (M+H)+ (C20H24N8O4 requires 441.1999).

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationThe mixture was concentrated
  3. filtrationthe desired product was filtered
  4. washrinsed with cold H2O

Sources & evidence

ORD record
ord-1458741edebd42a785df0b9e592ae9f0
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

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