Hydrochloric Acid → HCID 22046406, compound

HRID 1830740Notes

Reaction equation

HRID 1830740 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) δ8.62 (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-5f4f819fa6e444c582d15b85794f9fef
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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