Potassium Hydroxide → HCID 9823662, compound

HRID 1274138Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

Potassium hydroxide (1.18 g, 21.1 mmol) was added to a solution of (3) (0.5 g, 1.05 mmol) in MeOH/H2O (20 mL, 10%; v/v). The reaction mixture was heated to 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 0.46 g (quantitative yield) of the title compound: 1H NMR (DMSO) δ 12.36 (br s, 1H), 9.56 (br s, 1H), 8.78 (br s, 2H), 8.36 (s, 1H), 8.07 (d, 1H, J=9.2), 7.75 (s, 1H), 7.61 (s, 1H), 7.11 (d, 1H, J=9.3), 4.64 (m, 2H), 4.29 (m, 1H), 3.85 (s, 3H), 3.83 (s, 3H), 3.37 (m, 2H), 2.12 (m, 2H), 1.60 (m, 2H); 13C NMR (DMSO) δ 164.7, 161.3, 155.2, 154.4, 151.0, 146.7, 141.8, 140.1, 136.3, 115.2, 112.4, 105.2, 101.6, 99.3, 56.3, 56.0, 48.4, 43.3, 30.4; HRMS (FAB) m/z 425.1948 (M+H)+ (C21H24N6O4 requires 425.1937); Anal. (C21H24N6O4 ·2HCl·2H2O) C, H, N.

Workup

temperaturecooled to room temperature
concentrationThe mixture was concentrated
filtrationthe desired product was filtered
washrinsed with cold H2O

Sources & evidence

ORD record: ord-65d543f584ee417693303bfd9445e870
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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