3-(Morpholin-4-yl)aniline → [7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3-morpholin-4-yl-phenyl)-amine

HRID 1261941Notes

Reaction equation

HRID 1261941 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)[N:6]2[N:5]=1)=O.[N:23]1([C:29]2[CH:30]=[C:31]([NH2:35])[CH:32]=[CH:33][CH:34]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>COCCO>[CH3:22][S:19]([C:15]1[CH:14]=[C:13]([C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([NH:35][C:31]4[CH:32]=[CH:33][CH:34]=[C:29]([N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)[CH:30]=4)=[N:5]3)=[CH:10][CH:11]=2)[CH:18]=[CH:17][CH:16]=1)(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 8477683-(Morpholin-4-yl)anilineHCID 667114002-Methanesulfinyl-7-(3-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711532[7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3-morpholin-4-yl-phenyl)-amineYield 29.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

2-Methanesulfinyl-7-(3-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (125.0 mg, 0.0003727 mol) and 3-Morpholin-4-yl-phenylamine (183 mg, 0.00103 mol) were dissolved in 2-Methoxyethanol (3.2 mL) and the reaction was microwaved at 300 W 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 provide 50.00 mg of [7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(3-morpholin-4-yl-phenyl)-amine as a lyophilated powder. (M+H)=450.15. 1H NMR (400 MHz, DMSO, d6) δ 9.40 (s, 1H), 9.04 (s, 1H), 8.51 (m, 2H), 7.95 (d, 1H, J=7.88 Hz), 7.80 (d, 1H, J=8.05 Hz), 7.34 (d, 1H, J=8.09 Hz), 7.26 (d, 1H, J=4.72 Hz), 7.22 (m, 2H), 6.99 (d, 1H, J=4.72 Hz), 6.61 (m, 1H), 3.68 (m, 4H), 3.28 (s, 3H), 2.99 (m, 4H).

Workup

  1. customthe reaction was microwaved at 300 W at 180° C. until HPLC
  2. customconsumption of starting material
  3. customthe product was isolated
  4. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-877a1fb9ec1742d1813664c63906348c
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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