HCID 59248338, compound → HCID 178511949, compound

HRID 1622166Notes

Reaction equation

[C:1]([C:4]1[CH:33]=[CH:32][C:7]2[NH:8][C:9]([C:11]3[CH:12]=[C:13]([C:29](O)=[O:30])[CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([S:24](=[O:27])(=[O:26])[NH2:25])[CH:21]=[CH:20][C:19]=4[OH:28])[C:16]=3[OH:17])=[N:10][C:6]=2[CH:5]=1)(=[NH:3])[NH2:2].[NH2:34][CH2:35][CH2:36][S:37]([O-:40])(=[O:39])=[O:38].[Li+]>>[C:1]([C:4]1[CH:33]=[CH:32][C:7]2[NH:8][C:9]([C:11]3[CH:12]=[C:13]([C:29]([NH:34][CH2:35][CH2:36][S:37]([OH:40])(=[O:39])=[O:38])=[O:30])[CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([S:24](=[O:27])(=[O:26])[NH2:25])[CH:21]=[CH:20][C:19]=4[OH:28])[C:16]=3[OH:17])=[N:10][C:6]=2[CH:5]=1)(=[NH:3])[NH2:2]

Participants

Reactant 2

HCID 59248338HCID 59248338, compound

HCID 178511951HCID 178511951, compound

Product 1

HCID 178511949HCID 178511949, compound

Procedure

Proceeding as in Example 17, but substituting 5-(5-carbamimidoyl-1H-benzoimidazol-2-yl)-6,2′-dihydroxy-5′-sulfamoylbiphenyl-3-carboxylic acid (20 mg, 40 μmol), prepared as in Reference 10, and lithium 2-aminoethanesulfonate, prepared as in Reference 4, gave 2-{[5-(5-carbamimidoyl-1H-benzoimidazol-2-yl)-6,2′-dihydroxy-5′-sulfamoyl-biphenyl-3-carbonyl]-amino}-ethanesulfonic acid as a yellow solid, Compound 111. RP-HPLC (1-90S) RT=2.21 min; 1H NMR (400 MHz, d6-DMSO, selected signals): δ 9.36* (2H, s), 8.98* (2H, s), 8.74 (1H, J=1.6 Hz), 8.74 (1H, d, J=2.0 Hz), 8.49* (1H, br t, J=5.0 Hz), 8.17 (1H, s), 7.85 (1H, d, J=8.4 Hz), 7.81 (1H d, J=2.0 Hz), 7.75 (1H, dd, J=8.4 Hz, 0.8 Hz), 7.70 (1H, dd, J=2.4 Hz), 7.67 (1H, dd, J=8.4, 2.4 Hz); 7.16* (211, br s), 7.07 (1H, d, J=8.4 Hz); m/z (LCMS-ESI): Q+ 575 (M+H); Q− 573 (M−H).

Sources & evidence

ORD record: ord-ca15bd9e95e343a8a2248c8c04da7abe
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778625B2

Reaction notes

Loading…