Hydrochloric Acid → Amino-acetic acid 4-[4-amino-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2ylamino]-benzyl ester

HRID 1591627

Reaction equation

HRID 1591627 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH:16][C:17]2[CH:35]=[CH:34][C:20]([CH2:21][O:22][C:23](=[O:33])[CH2:24][NH:25]C(OC(C)(C)C)=O)=[CH:19][CH:18]=2)[N:3]=1.ClCCl.Cl.C(OCC)(=O)C>O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH:16][C:17]2[CH:35]=[CH:34][C:20]([CH2:21][O:22][C:23](=[O:33])[CH2:24][NH2:25])=[CH:19][CH:18]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 690158312-Tert-butoxycarbonylamino-acetic acid 4-[4-amino-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-yl-amino]-benzyl ester

Product 1

HCID 10135531Amino-acetic acid 4-[4-amino-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2ylamino]-benzyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-tert-butoxycarbonylamino-acetic acid 4-[4-amino-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2yl-amino]-benzyl ester (1.0 g, 2 mmol), dichloromethane (20 ml), and a solution of hydrogen chloride in 1,4-dioxane (4 M, 5 ml) was stirred for 12 hours. The reaction mixture was poured into ethyl acetate (100 ml). The solid filtered and dried under reduced pressure to provide the hydrochloride salt of the title compound (0.38 g, 84% yield). 1H NMR (CD3OD) δ7.75-8 (br s, 2H), 7.74 (s, 1H), 7.56-7.43 (m, 6H), 5.36 (s, 2H) 3.67 (s, 2H) 2.58 (s, 3H).

Workup

  1. filtrationThe solid filtered
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-19714d18a2f84310a51549d81fa87e12
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Linked notes

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