Hydrochloric Acid → HCID 44553509, compound

HRID 1663170Notes

Reaction equation

HRID 1663170 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([CH2:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24](=[O:36])[NH:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=2)[CH:13]=[CH:12][N:11]=1)=[O:8])C.[OH-].[Na+].O.Cl>CO>[C:34]([C:31]1[CH:32]=[CH:33][C:28]([CH2:27][O:26][NH:25][C:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][CH2:16][C:14]2[CH:13]=[CH:12][N:11]=[C:10]([NH:9][C:7](=[O:8])[NH:6][CH2:5][C:4]([OH:37])=[O:3])[CH:15]=2)=[O:36])=[CH:29][CH:30]=1)#[N:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 44553507[3-(4-{[2-(4-Cyano-benzyloxycarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-ureido]-acetic acid ethyl ester

Product 1

HCID 44553509HCID 44553509, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of [3-(4-{[2-(4-cyano-benzyloxycarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-ureido]-acetic acid ethyl ester (Example 529, 188 mg) in methanol (4 ml) was added 2 M aqueous sodium hydroxide (2 ml). The reaction mixture was stirred at room temperature for 15 minutes. Water (6 ml) was added and the pH of the mixture was adjusted to 5 by addition of 4 M hydrochloric acid. The resulting precipitated material was isolated by filtration and dried under high vacuum, affording the title compound. 13C-NMR (DMSO-d6) δ 171.7, 167.5, 154.7, 153.5, 151.3, 148.4, 146.7, 141.9, 132.6, 132.1, 129.1, 128.0, 118.7, 115.3, 114.8, 112.8, 111.5, 110.7, 109.2, 75.9, 45.3, 41.4

Workup

  1. customThe resulting precipitated material
  2. customwas isolated by filtration
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-89df306c0a4f4910ab82b034f048790c
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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