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

HRID 1435758

Reaction equation

HRID 1435758 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-2-yl-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) δ 7.75-8 (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-19da8372567049a9b8860173349e541e
Source dataset
uspto-grants-2009_11
Patent number
US07618968B2

Linked notes

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