2-Methoxyethanol → N-[7-(3-Chloro-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-N',N'-dimethyl-benzene-1,3-diamine

HRID 1261930Notes

Reaction equation

HRID 1261930 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14](S(C)=O)=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[CH3:29][N:30]([CH3:38])[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[CH:32]=1.COCCO>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([NH:37][C:33]4[CH:34]=[CH:35][CH:36]=[C:31]([N:30]([CH3:38])[CH3:29])[CH:32]=4)=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 76084N,N-dimethyl-m-phenylenediamineHCID 81531DiisopropylethylamineHCID 66710773HCID 66710773, compound

Product 1

HCID 66710978N-[7-(3-Chloro-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-N',N'-dimethyl-benzene-1,3-diamineYield 3.9%

Conditions

Temperature
180 °C

Procedure

7-(3-Chloro-phenyl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (76.2 mg, 0.000261 mol), N,N-Diisopropylethylamine (0.0682 mL, 0.000392 mol) and N,N-Dimethyl-benzene-1,3-diamine (71.1 mg, 0.000522 mol) were dissolved in 2-Methoxyethanol (1.83 mL, 0.0232 mol) and the reaction was heated at 180° C. until HPLC showed consumption of starting material. The reaction mixture was then reduced en vacuo and the product was isolated and purified by Gilson prep HPLC to afford 3.73 mg of N-[7-(3-Chloro-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-N′,N′-dimethyl-benzene-1,3-diamine as a lyophilated powder. (M+H)=364.11. 1H NMR (400 MHz, CDCl3) δ 9.08 (s, 1H), 8.37 (d, 1H, J=9.60 Hz), 8.10 (s, 1H), 7.89 (d, 1H, J=7.58 Hz), 7.44 (m, 3H), 7.20 (d, 1H, J=4.80 Hz), 7.03 (d, 1H, J=4.54 Hz), 6.61 (m, 2H), 3.11 (s, 6H).

Workup

  1. customconsumption of starting material
  2. customthe product was isolated
  3. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-43f0daa2fec84b7c86d0f06e0ba35180
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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