Hydrochloric Acid → HCID 59490928, compound

HRID 1952224Notes

Reaction equation

HRID 1952224 reaction equation
C([O:3][C:4]([C:6]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:13]2[C:8](=[N:9][C:10]([CH3:23])=[CH:11][CH:12]=2)[C:7]=1[C:24]1[C:25]([O:30][CH3:31])=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:5])C.[OH-].[Li+].Cl>O1CCCC1>[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][N:14]1[C:13]2[C:8](=[N:9][C:10]([CH3:23])=[CH:11][CH:12]=2)[C:7]([C:24]2[C:25]([O:30][CH3:31])=[N:26][CH:27]=[CH:28][CH:29]=2)=[C:6]1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59490939HCID 59490939, compound

Product 1

HCID 59490928HCID 59490928, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Compound B4 was diluted with tetrahydrofuran (3 mL) and to the resulting solution was added 1M aqueous lithium hydroxide (2 mL, excess). The reaction was heated to 70° C. and allowed to stir at this temperature for 14 hours. The reaction was then acidified using 1M HCl, and extracted several times with ethyl acetate. The organic layer was collected and concentrated in vacuo to provide 1-(2-Fluoro-benzyl)-3-(2-methoxy-pyridin-3-yl)-5-methyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid B5 (0.2 g, 80% yield). MS: 392.16 (M+H)+.

Workup

  1. extractionextracted several times with ethyl acetate
  2. customThe organic layer was collected
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a64bdb1c732c4ce5a34194bf812ea673
Source dataset
uspto-grants-2013_03
Patent number
US08404845B2

Reaction notes

Loading…