Diisopropylethylamine → (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-(3-morpholin-4-yl-phenyl)-amine

HRID 1261937Notes

Reaction equation

HRID 1261937 reaction equation
BrC1N2C(C=NC(S(C)=O)=N2)=CC=1.[Br:14][C:15]1[N:23]2[C:18]([CH:19]=[N:20][C:21]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[CH:26]=3)=[N:22]2)=[CH:17][CH:16]=1.N1(C2C=C(N)C=CC=2)CCOCC1.C(N(CC)C(C)C)(C)C>COCCO>[Br:14][C:15]1[N:23]2[C:18]([CH:19]=[N:20][C:21]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[CH:26]=3)=[N:22]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 8477683-(Morpholin-4-yl)anilineHCID 66711760(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-(3-morpholin-4-yl-phenyl)-amine 7-Bromo-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711115(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-(3-morpholin-4-yl-phenyl)-amineYield 48.6%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-(3-morpholin-4-yl-phenyl)-amine 7-Bromo-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (2.00 g, 0.00769 mol), 3-Morpholin-4-yl-phenylamine (1.37 g, 0.00769 mol) and N,N-Diisopropylethylamine (1.49 g, 0.0115 mol) were dissolved in 2-Methoxyethanol (13.7 mL). The reaction was microwaved on 300 watts, 180° C. for 80 minutes. The solvent was then removed en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 1.40 g of (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-(3-morpholin-4-yl-phenyl)-amine as a brown solid. (M+H)=376.05.

Workup

  1. customThe reaction was microwaved on 300 watts, 180° C. for 80 minutes
  2. customThe solvent was then removed en vacuo
  3. customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)

Sources & evidence

ORD record
ord-50b357f57981437dbf06dad785849a5e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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