Isoluminol → HCID 59479520, compound

HRID 1515511Notes

Reaction equation

HRID 1515511 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:11][CH:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[C:13]([OH:15])=[O:14])[CH:7]=[CH:8][C:9]=1F)(=[O:3])[NH2:2].NC1C=C2C(=CC=1)[C:33](=[O:37])[NH:32]NC2=O.COC1C=C(B(O)O)C=CC=1OC.O.C(O)(=O)C=O>>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([CH:12]([NH:11][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[C:33](=[O:37])[NH:32][NH:2][C:1]3=[O:3])[C:13]([OH:15])=[O:14])[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

5

Reactant 4

HCID 95014IsoluminolHCID 27347023,4-Dimethoxyphenylboronic acidHCID 15620607Glyoxylic acid, monohydrateHCID 594793922-(3-Carbamoyl-4-fluorophenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

Product 1

HCID 59479520HCID 59479520, compoundYield 95%

Procedure

15A was prepared in a procedure similar to that of 13A using 6-amino-2,3-dihydrophthalazine-1,4-dione, 3,4-dimethoxyphenylboronic acid and glyoxylic acid monohydrate. Yield: 95%. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.73 (s, 3H) 3.74 (s, 3H) 5.15 (d, J=7.03 Hz, 1H) 6.95 (d, 1H) 7.01-7.06 (m, 1H) 7.13 (d, J=2.20 Hz, 1H) 7.25 (d, J=7.03 Hz, 2H) 7.74 (s, 1H), LCMS: 344 (M+1).

Sources & evidence

ORD record
ord-c6bc909f9a9744d78b2a1d40ce22d8d5
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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