Hydrochloric Acid → HCID 22046406, compound

HRID 1821756Notes

Reaction equation

HRID 1821756 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=2)=[O:12])=[C:6]([O:21][CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH:5]=1.[OH-].[Li+].Cl>CO>[CH3:27][N:25]([CH3:26])[CH2:24][CH2:23][CH2:22][O:21][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[NH:10][C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12])[C:3]([OH:28])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67256058HCID 67256058, compound

Product 1

HCID 22046406HCID 22046406, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-(3-dimethylamino-propoxy)-4-[3-(5-methyl-pyrazin-2-yl)-ureido]-benzoic acid methyl ester (1.0 gm; 3.3 mmol) in methanol (25 mL) was added lithium hydroxide (5 mL of a 2M aqueous solution). The reaction was heated to 60 degrees and stirred for 12 hours. The reaction was allowed to cool to room temperature and the pH was adjusted to 5.5 with 1N hydrochloric acid. A precipitate formed which was filtered and dried under reduced pressure to yield the desired product as a tan solid (52% yield). 1H-NMR (400 MHz, d6-DMSO) δ 8.62 (br s, 1H), 8.39 (d, 1H), 8.21 (s, 1H), 7.59 (d, 1H), 7.43 (s, 1H), 4.15 (t, 2H), 2.42 (m, 5H), 2.18 (s, 6H), 2.01 (m, 2H).

Workup

  1. temperatureThe reaction was heated to 60 degrees
  2. customA precipitate formed which
  3. filtrationwas filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4cc836710c9043f5bd9dd4c7d2d8f721
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

Loading…