Lithium Hydroxide → 6'-{[(Ethylamino)carbonyl]amino}-4'-(4-phenyl-1,3-thiazol-2-yl)-3,3'-bipyridine-5-carboxylic acid

HRID 2243037Notes

Reaction equation

HRID 2243037 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[CH:18]=2)=[C:9]([C:24]2[S:25][CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:28]=2)[CH:8]=1)=[O:5])[CH3:2].[Li+].[OH-].C(#N)C>C1COCC1>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[CH:18]=2)=[C:9]([C:24]2[S:25][CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:28]=2)[CH:8]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6342AcetonitrileHCID 59208481Ethyl 6'-{[(ethylamino)carbonyl]amino}-4'-(4-phenyl-1,3-thiazol-2-yl)-3,3'-bipyridine-5-carboxylate

Product 1

HCID 592083416'-{[(Ethylamino)carbonyl]amino}-4'-(4-phenyl-1,3-thiazol-2-yl)-3,3'-bipyridine-5-carboxylic acidYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 25 mL round-bottomed flask ethyl 6′-{[(ethylamino)carbonyl]amino}-4′-(4-phenyl-1,3-thiazol-2-yl)-3,3′-bipyridine-5-carboxylate (Example 131, 0.20 g, 0.42 mmol) was suspended in THF (3 mL). 1N LiOH (1.20 mL, 1.21 mmol) was added and the solution was stirred at room temperature over night. The solvent was removed and the resulting residue was diluted with water. The pH was adjusted to 4 (pH paper) with 2N HCl. White solids formed. They were trichurated with acetonitrile for 30 minutes and then filtered, washed with acetonitrile and dried in vacuo to give 58 mg of the title compound. LC/MS (ES+)[(M+H)+]: 446 for C23H11N5O3S. 1H NMR (300 MHz, d6-DMSO): 1.10 (t, 3H), 3.21 (m, 2H), 7.32-7.40 (m, 3H), 7.65 (t, 1H), 7.70 (s, 1H), 7.72 (s, 1H), 8.22 (s, 1H), 8.23-8.26 (m, 2H), 8.31 (s, 1H), 8.73 (d, 1H), 9.08 (d, 1H), 9.45 (s, 1H).

Workup

  1. customThe solvent was removed
  2. additionthe resulting residue was diluted with water
  3. customWhite solids formed
  4. filtrationfiltered
  5. washwashed with acetonitrile
  6. customdried in vacuo

Sources & evidence

ORD record
ord-43f4a265718c4ffb8cc00aa8287b7bae
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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