Water → HCID 22346432, compound

HRID 897303Notes

Reaction equation

HRID 897303 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12](/[CH:21]=[CH:22]/[C:23]([O:25]C)=O)[N:11]=2)=[O:9])=[CH:4][CH:3]=1.[NH2:29][CH2:30][CH2:31][SH:32].O>CN(C=O)C>[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([CH:21]3[S:32][CH2:31][CH2:30][NH:29][C:23](=[O:25])[CH2:22]3)[N:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6058CysteamineHCID 20816871HCID 20816871, compound

Product 1

HCID 22346432HCID 22346432, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl (2E)-3-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy[1,6]-naphthyridin-5-yl)-2-propenoate (Example 137, Step 1) (1.22 g, 3.20 mmol) and cysteamine (4.0 g) in DMF (15 mL) was heated in an oil bath at 80° C. under an atmosphere of nitrogen with stirring for 18 hours. The product mixture was treated with water and the mixture was acidified to pH 2. The resultant precipitate was filtered, dissolved in DMSO, and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound as yellow solid.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. dissolutiondissolved in DMSO
  3. customsubjected to HPLC purification on C-18 stationary phase
  4. washeluted with water/acetonitrile/TFA mobile phase
  5. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-78caed494bd74b35a49460b2ee7f7d7d
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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