HCID 9893021, compound → HCID 9847446, compound

HRID 1274139Notes

Reaction equation

C([O:5][C:6](=[O:38])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:29]=[C:28]([NH2:30])[C:27]4[C:22](=[CH:23][C:24]([O:33][CH3:34])=[C:25]([O:31][CH3:32])[CH:26]=4)[N:21]=3)[CH2:16][CH2:15]2)=[C:9]([N+:35]([O-:37])=[O:36])[CH:8]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:30][C:28]1[C:27]2[C:22](=[CH:23][C:24]([O:33][CH3:34])=[C:25]([O:31][CH3:32])[CH:26]=2)[N:21]=[C:20]([N:17]2[CH2:18][CH2:19][CH:14]([NH:13][C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:38])=[O:5])=[CH:8][C:9]=3[N+:35]([O-:37])=[O:36])[CH2:15][CH2:16]2)[N:29]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of (6) (0.03 g, 0.057 mmol) in TFA (5 mL) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was evaporated to a pale yellow solid residue (0.026 g, 78 %); 1H NMR (DMSO) δ 11.75 (br s, 1H), 8.81 (s, 1H), 8.69 (s, 1H), 8.61 (d, 1H, J=1.9), 8.24 (d, 1H, J=7.7), 7.99 (d, 1H, J=7.3), 7.67 (s, 1H), 7.34 (d, 1H, J=9.3), 7.20 (s, 1H), 4.49 (d, 2H, J=13.2), 4.11 (m, 1H), 3.89 (s, 3H), 3.83 (s, 3H), 3.37 (t, 2H, J=11.8), 2.12 (d, 2H, J=10.3), 1.76 (m, 2H); 13C NMR (DMSO) δ 165.8, 161.4, 157.8, 155.4, 151.2, 146.8, 146.2, 136.1, 130.6, 128.6, 117.5, 115.0, 104.8, 101.6, 98.8, 56.1, 56.0, 48.8, 43.3, 30.4; HRMS (FAB) m/z 469.1816 (M+H)+ (C22H24N6O6 requires 469.1830); Anal. (C22H24N6O6 ·11/2CF3COOH·11/4H2O·1/4CH3OH) C, H, N.

Workup

customThe reaction mixture was evaporated to a pale yellow solid residue (0.026 g, 78 %)

Sources & evidence

ORD record: ord-7ac6d696ac524ecaa7244b0fe26833bb
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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