Nicotinic Acid → HCID 131722411, compound

HRID 1530940Notes

Reaction equation

HRID 1530940 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Li+].[OH-].N1C=CC=C(CC([N:21]2[CH2:28][S:27][CH2:26][C@@H:22]2[C:23]([OH:25])=[O:24])=O)C=1.[CH2:29]([O:36][C:37]1[CH:48]=[CH:47][C:40]([CH2:41][C@@H:42]([C:44]([OH:46])=[O:45])[NH2:43])=[CH:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1]([N:21]2[CH2:28][S:27][CH2:26][C@@H:22]2[C:23]([OH:25])=[O:24])=[O:9])[CH:3]=1.[CH2:29]([O:36][C:37]1[CH:38]=[CH:39][C:40]([CH2:41][C@@H:42]([C:44]([OH:46])=[O:45])[NH2:43])=[CH:47][CH:48]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 938Nicotinic AcidHCID 3939Lithium HydroxideHCID 131722412HCID 131722412, compound

Product 1

HCID 131722411HCID 131722411, compound

Procedure

Intermediate 18 was coupled to nicotinic acid in a similar manner to that described for Intermediate 19, and subsequently hydrolysed with aqueous LiOH, as described for the compound of Example 7, to afford the title compound. δH (DMSO-d6) 8.78-8.55 (2 H, br m), 8.38 (1 H, br d J 7.8 Hz), 8.21-7.25 (7 H, m), 7.11 (2 H, d, J 8.5 Hz), 6.85 (2 H, br d, J 8.0 Hz), 5.02 (2H, s), 5.03-4.3 (4 H, m), 3.40-3.22 (1 H, br m), 3.03 (1 H, dd, J 13.8, 4.6 Hz) and 2.90-2.75 (2 H, m); m/z (ESI), 492 (MH+).

Sources & evidence

ORD record
ord-24fef29860654c7aa84ca554ac010ec5
Source dataset
uspto-grants-2001_03
Patent number
US06197794B1

Reaction notes

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