4-Aminocarbonylphenylboronic acid → Fen1-IN-2

HRID 550715Notes

Reaction equation

HRID 550715 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][N:6]1[C:11]2[CH:12]=[CH:13][S:14][C:10]=2[C:9](=[O:15])[N:8]([OH:16])[C:7]1=[O:17].[NH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23]>>[OH:16][N:8]1[C:9](=[O:15])[C:10]2[S:14][CH:13]=[CH:12][C:11]=2[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([C:27]3[CH:28]=[CH:29][C:24]([C:22]([NH2:21])=[O:23])=[CH:25][CH:26]=3)[CH:20]=[CH:19][CH:18]=2)[C:7]1=[O:17]

Participants

3

Reactant 2

HCID 27378114-Aminocarbonylphenylboronic acidHCID 115448741-(3-Bromo-benzyl)-3-hydroxy-1H-thieno[3,2-d]pyrimidine-2,4-dione

Product 1

HCID 11654052Fen1-IN-2

Procedure

The title compound was prepared from 1-(3-Bromo-benzyl)-3-hydroxy-1H-thieno[3,2-d]pyrimidine-2,4-dione (from previous example) and 4-aminocarbonyl-phenyl boronic acid via general procedure C. The crude product was purified by mass-triggered preparative HPLC. 1H NMR (DMSO-d6) δ 10.87 (bs, 1H), 8.11 (d, 1H, J=5.4 Hz), 7.96 (d, 2H, J=8.4 Hz), 7.74 (s, 1H), 7.71 (d, 2H, J=7.8 Hz), 7.63 (d, 1H, J=7.8 Hz), 7.45 (t, 1H, J=7.8 Hz), 7.36 (d, 1H, J=5.4 Hz), 7.28 (d, 1H, J=7.5 Hz), 5.35 (s, 2H); Electrospray MS: 394 (M+H); retention time: 1.96 min.

Workup

  1. customThe crude product was purified by mass-triggered preparative HPLC

Sources & evidence

ORD record
ord-673908b078eb411c9f932d16dfae76ee
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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