3,4-Dimethoxyphenylboronic acid → HCID 59479434, compound

HRID 1515573Notes

Reaction equation

HRID 1515573 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=1F)(=[O:3])[NH2:2].[NH2:26]C1C=CN=C(C(N)=O)C=1.COC1C=C(B(O)O)C=CC=1OC.O.C(O)(=O)C=O>>[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][N:26]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 4

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 15620607Glyoxylic acid, monohydrateHCID 231312624-Aminopyridine-2-carboxamideHCID 594793922-(3-Carbamoyl-4-fluorophenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

Product 1

HCID 59479434HCID 59479434, compoundYield 63%

Procedure

99C was prepared in a procedure similar to that of 13A using 99B, 3,4-dimethoxyphenylboronic acid and glyoxylic acid monohydrate. Yield: 63%. 1H NMR (400 MHz, Methanol-d4) δ ppm 3.83 (s, 3H) 3.84 (s, 3H) 5.45 (s, 1H) 6.95-7.01 (m, 2H) 7.05-7.11 (m, 3H) 8.11 (d, J=6.59 Hz, 1H); LCMS: 331 (M+1).

Sources & evidence

ORD record
ord-5afb5706e8054e3a9709256382c52178
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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