Lithium Hydroxide → HCID 86305421, compound

HRID 712712Notes

Reaction equation

HRID 712712 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[N:14][C:15]3[N:16]([C:22](=[O:24])[NH2:23])[CH2:17][CH2:18][CH2:19][C:20]=3[CH:21]=2)[CH:11]=1)C.[OH-].[Li+]>CCO.O>[C:22]([N:16]1[C:15]2[N:14]=[CH:13][C:12]([C:10]3[CH:11]=[C:6]([CH2:5][C:4]([OH:25])=[O:3])[CH:7]=[N:8][CH:9]=3)=[CH:21][C:20]=2[CH2:19][CH2:18][CH2:17]1)(=[O:24])[NH2:23]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 117667090HCID 117667090, compound

Product 1

HCID 86305421HCID 86305421, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of [5-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-yl]-acetic acid ethyl ester (1.0 g, 2.9 mmol) and lithium hydroxide (123 mg, 5.1 mmol) in EtOH (10 mL) and H2O (10 mL) are stirred at room temperature for 16 h. The reaction is concentrated to remove the EtOH and the remaining aqueous mixture is treated with 1N HCl and diluted with EtOAc. The solid formed is filtered, rinsed and dried to give 500 mg of the titled product.

Workup

  1. concentrationThe reaction is concentrated
  2. customto remove the EtOH
  3. additionthe remaining aqueous mixture is treated with 1N HCl
  4. additiondiluted with EtOAc
  5. customThe solid formed
  6. filtrationis filtered
  7. washrinsed
  8. customdried

Sources & evidence

ORD record
ord-fb72ba09d76f434db7ff3f858a07cc1a
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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