Glyoxylic acid, monohydrate → 2-(1,3-Dioxoisoindolin-5-ylamino)-2-(4-fluoro-3-methoxyphenyl)acetic acid

HRID 1515528Notes

Reaction equation

HRID 1515528 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][CH:11]([C:15]2[CH:20]=[CH:19][C:18](OC)=[C:17]([O:23][CH3:24])[CH:16]=2)[C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2].N=C1C=CC2C(=O)N[C:29](=[O:36])C=2C1.COC1C=C(B(O)O)C=CC=1[F:45].O.C(O)(=O)C=O>>[O:36]=[C:29]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][CH:11]([C:15]3[CH:20]=[CH:19][C:18]([F:45])=[C:17]([O:23][CH3:24])[CH:16]=3)[C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[C:1](=[O:3])[NH:2]1

Participants

5

Reactant 4

HCID 15620607Glyoxylic acid, monohydrateHCID 44558185(4-Fluoro-3-methoxyphenyl)boronic acidHCID 598380342-(3-Carbamoylphenylamino)-2-(3,4-dimethoxyphenyl)acetic acidHCID 681067335-Iminoisoindoline-1,3-dione

Product 1

HCID 594795222-(1,3-Dioxoisoindolin-5-ylamino)-2-(4-fluoro-3-methoxyphenyl)acetic acidYield 17%

Procedure

43A was prepared in a procedure similar to that of 1A using 5-iminoisoindoline-1,3-dione, 7C and glyoxylic acid monohydrate. Yield: 17%. 1H NMR (400 MHz, Methanol-d4) δ ppm 3.87 (s, 3H) 5.21 (s, 1H) 6.90 (dd, J=8.35, 2.20 Hz, 1H) 6.99 (d, J=1.76 Hz, 1H) 7.06-7.12 (m, 2H) 7.28 (d, J=8.79 Hz, 1H) 7.51 (d, J=8.35 Hz, 1H), LCMS: 345 (M+1).

Sources & evidence

ORD record
ord-46763461ceaa4ecfa8497aaf11c3d181
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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