Hydrochloric Acid → N-(4-Cyano-benzyloxy)-2-({2-[3-(2-hydroxy-ethyl)-ureido]-pyridin-4-ylmethyl}-amino)-benzamide

HRID 1663173Notes

Reaction equation

HRID 1663173 reaction equation
[C:1]([C:3]1[CH:39]=[CH:38][C:6]([CH2:7][O:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=[O:37])[NH:28][CH2:29][CH2:30][O:31]C(=O)C(C)=C)[CH:21]=2)=[O:11])=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].Cl.O>CO>[C:1]([C:3]1[CH:39]=[CH:38][C:6]([CH2:7][O:8][NH:9][C:10](=[O:11])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]([NH:28][CH2:29][CH2:30][OH:31])=[O:37])[CH:21]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 445543602-Methyl-acrylic acid 2-[3-(4-{[2-(4-cyano-benzyloxycarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-ureido]-ethyl ester

Product 1

HCID 44554190N-(4-Cyano-benzyloxy)-2-({2-[3-(2-hydroxy-ethyl)-ureido]-pyridin-4-ylmethyl}-amino)-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 2-methyl-acrylic acid 2-[3-(4-{[2-(4-cyanobenzyloxy-carbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-ureido]-ethyl ester (Example 533, 500 mg) in methanol (10 ml) was added 2 M aqueous sodium hydroxide (5 ml). The reaction mixture was stirred at room temperature for 20 minutes. The pH of the mixture was adjusted to 5 by addition of 4 M hydrochloric acid and water (15 ml) was added. The resulting precipitated material was isolated by filtration and dried in vacuo, and gave the title compound. 13C-NMR (DMSO-d6) δ 167.4, 154.8, 153.8, 151.1, 148.6, 146.7, 141.8, 132.6, 132.1, 129.1, 128.0, 118.6, 115.1, 114.8, 113.0, 111.6, 110.8, 109.3, 76.0, 60.2, 45.3, 41.8.

Workup

  1. additionwas added
  2. customThe resulting precipitated material
  3. customwas isolated by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5e9234667d8a40c6ac3b222d15b5dedc
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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