Potassium Hydroxide → HCID 9847749, compound

HRID 1274136Notes

Reaction equation

HRID 1274136 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)=[C:9]([Cl:36])[N:8]=1)=[O:6]>C(O)C>[NH2:13][C:12]1[C:7]([C:5]([OH:6])=[O:4])=[N:8][C:9]([Cl:36])=[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 9805525HCID 9805525, compound

Product 1

HCID 9847749HCID 9847749, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Potassium hydroxide (0.26 g, 4.7 mmol) was added to a solution of (1) (0.06 g, 0.123 mmol) in ethanol (2 mL) 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) (2 mL, 3M) and the desired product was filtered and rinsed with cold H2O to give 0.05 g (89%) of the title compound: 1H NMR (DMSO) δ 12.20 (br s, 1H), 8.50 (br s, 1H), 7.69 (s, 1H), 7.40 & 7.31 (br s, 2H), 7.16 (d, 1H, J=7.2), 4.70 (d, 2H, J=11.5), 4.24 (m, 1H), 3.86 (s, 3H), 3.82 (s, 3H), 3.10 (m, 2H), 1.92 (m, 2H), 1.66 (m, 2H); 13C NMR (DMSO) δ 167.4, 161.3, 155.7, 155.1, 150.6, 146.5, 119.0, 109.2, 104.8, 101.7, 56.2, 55.9, 47.7, 43.9, 30.4; HRMS (FAB) m/z 475.1589 (M+H)+ (C20H23N8O4Cl requires 475.1604); Anal. (C20H23N8O4Cl·2HCl·1/2H2O) C, H, N.

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-7753bbbfdec34f04ba7e2bef37c60713
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

Loading…