3,4-Dimethoxyphenylboronic acid → 2-(3-Carbamoyl-5-fluorophenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

HRID 1515559Notes

Reaction equation

HRID 1515559 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]=[C:8](C)[CH:9]=1)(=[O:3])[NH2:2].NC1C=C(C=C([F:36])C=1)C(N)=O.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]=[C:8]([F:36])[CH:9]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 4

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 15620607Glyoxylic acid, monohydrateHCID 468353333-Amino-5-fluorobenzamideHCID 594794972-(3-Carbamoyl-5-methylphenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

Product 1

HCID 594795072-(3-Carbamoyl-5-fluorophenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

Procedure

Using a procedure analogous to that described for the preparation of 89D, 91A was reacted with 3,4-dimethoxyphenylboronic acid and glyoxylic acid monohydrate to give 91B. 1H NMR (400 MHz, CD3OD) δ ppm 3.81 (s, 3H) 3.82 (s, 3H) 5.06 (s, 1H) 6.49 (d, J=11.43 Hz, 1H) 6.79 (d, J=9.23 Hz, 1H) 6.93 (d, J=8.35 Hz, 1H) 6.97 (s, 1H) 7.04-7.10 (m, 1H) 7.12 (s, 1H); LC/MS 349 (M+H).

Sources & evidence

ORD record
ord-2c94e869b3fc42aebddc29f1b6c9ed28
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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