Triethylamine → (1-{4-Methoxy-6-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-[1,3,5]triazin-2-yl}-piperidin-4-yl)-acetic acid ethyl ester

HRID 1942894Notes

Reaction equation

HRID 1942894 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:13]([O:23][CH3:24])[CH:12]=2)[N:3]=1.Cl.[CH2:26]([O:28][C:29](=[O:37])[CH2:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[CH3:27].C(N(CC)CC)C>CO>[CH2:26]([O:28][C:29](=[O:37])[CH2:30][CH:31]1[CH2:36][CH2:35][N:34]([C:2]2[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]4)=[C:13]([O:23][CH3:24])[CH:12]=3)[N:3]=2)[CH2:33][CH2:32]1)[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 45358839Piperidin-4-yl-acetic acid ethyl ester hydrochlorideHCID 86640783(4-Chloro-6-methoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

Product 1

HCID 45274964(1-{4-Methoxy-6-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-[1,3,5]triazin-2-yl}-piperidin-4-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of (4-chloro-6-methoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (100 mg, 0.29 mmol) and ethyl-2-(piperidin-4-yl)acetate hydrochloride (63 mg, 0.30 mmol) in 3 ml of methanol was treated with triethylamine (0.13 ml, 0.92 mmol). The mixture was stirred for 3 hours at room temperature, concentrated and the product purified by chromatography on silica gel using ethyl acetate as an eluent. The title compound was isolated as a colorless solid (137 mg, 99%).

Workup

  1. concentrationconcentrated
  2. customthe product purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b82cf8205ec94cc98d85bcbcfdf9bf80
Source dataset
uspto-grants-2013_03
Patent number
US08389717B2

Reaction notes

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