N,N-Dimethylethylenediamine → HCID 178483777, compound

HRID 449083Notes

Reaction equation

HRID 449083 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:31][CH:30]=3)[N:9]=[C:10]([CH:11]3[CH2:16][CH2:15][CH:14]([CH2:17]OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[CH3:42][N:43]([CH3:47])[CH2:44][CH2:45][NH2:46]>CO>[NH2:1][C:2]1[C:7]2=[C:8]([C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)=[CH:31][CH:30]=3)[N:9]=[C:10]([C@H:11]3[CH2:16][CH2:15][C@H:14]([CH2:17][NH:46][CH2:45][CH2:44][N:43]([CH3:47])[CH3:42])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 86636037HCID 86636037, compound

Product 1

HCID 178483777HCID 178483777, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of toluene-4-sulfonic acid 4-[4-amino-5-(4-phenoxy-phenyl)-imidazo[5,1-f][1,2,4]triazin-7-yl]-cyclohexylmethyl ester (5.0 mg, 0.0088 mmol), N,N-dimethyl-1,2-ethanediamine (1 mL, 0.009 mol) in MeOH (1 mL) was heated in microwave reactor at 300 watt, 100° C. for 2 h. The solvent and excess amine were removed in vacuo, and the material was purified by silica gel chromatography, eluting with 5% (7N NH3 in MeOH) in DCM. HPLC: tR=1.99 min. (OpenLynx, polar—5 min). MS (ES+): m/z 486.19 (100) [MH+].

Workup

  1. customThe solvent and excess amine were removed in vacuo
  2. customthe material was purified by silica gel chromatography
  3. washeluting with 5% (7N NH3 in MeOH) in DCM
  4. customHPLC: tR=1.99 min. (OpenLynx, polar—5 min)

Sources & evidence

ORD record
ord-8e0d33d290fd44ceaa474f1009fe1631
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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