HCID 9827071, compound → HCID 9932845, compound

HRID 1274141Notes

Reaction equation

HRID 1274141 reaction equation
C([O:5][C:6](=[O:36])[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]([O:30][CH3:31])[C:27]4[C:22](=[CH:23][C:24]([O:34][CH3:35])=[C:25]([O:32][CH3:33])[CH:26]=4)[N:21]=3)[CH2:16][CH2:15]2)=[CH:9][CH:8]=1)(C)(C)C>FC(F)(F)C(O)=O>[CH3:31][O:30][C:28]1[C:27]2[C:22](=[CH:23][C:24]([O:34][CH3:35])=[C:25]([O:32][CH3:33])[CH:26]=2)[N:21]=[C:20]([N:17]2[CH2:18][CH2:19][CH:14]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([C:6]([OH:36])=[O:5])=[CH:12][CH:11]=3)[CH2:15][CH2:16]2)[N:29]=1

Participants

3

Reactant 1

HCID 9827071HCID 9827071, compound

Product 1

HCID 9932845HCID 9932845, compoundYield 140.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (14) (0.062 g, 0.13 mmol) in trifluoroacetic acid (3 mL) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was evaporated to a light brown oily residue (0.08 g, quantitative yield); 1H NMR (DMSO) δ 7.68 (d, 2H, J=8.7), 7.25 (s, 1H), 7.23 (s, 1H), 6.66 (d, 2H, J=8.7), 4.54 (d, 2H, J=12.0), 4.15 (s, 3H), 3.91 (s, 3H), 3.85 (s, 3H), 3.73 (m, 1H), 3.45 (t, 2H, J=12.0), 2.10 (m, 2H), 1.53 (m, 2H): 13C NMR (DMSO) δ 167.5, 156.5, 151.4, 149.7, 148.9, 147.1, 131.2, 117.0, 111.2, 106.1, 103.0, 102.8, 101.1, 56.2, 55.9, 55.3, 47.9, 43.7, 30.9; HRMS (FAB) m/z 439.2001 (M+H)+ (C23H26N4O5 requires 439.1981); Anal. (C23H26N4O5 ·1CF3COOH·1/2H2O) C, H, N.

Sources & evidence

ORD record
ord-8377d7b164224a259762a0def00ba97e
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

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