1-Methoxy-2-propanol → n-{2-[2-(4-Morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide

HRID 1262034Notes

Reaction equation

HRID 1262034 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]=[CH:15][C:14]=3[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[N:6]2[N:5]=1)=O.[CH2:24]1[N:29]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:28][CH2:27][O:26][CH2:25]1.C(N(CC)C(C)C)(C)C.COCC(O)C>>[N:29]1([C:30]2[CH:31]=[CH:32][C:33]([NH:36][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=5[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[N:6]4[N:5]=3)=[CH:34][CH:35]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 81531DiisopropylethylamineHCID 66711409N-[2-(2-methylsulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide

Product 1

HCID 66711711n-{2-[2-(4-Morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamideYield 77.4%

Procedure

N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide (100.0 mg, 0.2854 mmol), 4-(4-morpholino)aniline (102 mg, 0.571 mmol) and N,N-Diisopropylethylamine (0.149 mL, 0.856 mmol) were dissolved in 1-Methoxy-2-propanol (1.08 mL, 11.1 mmol). The reaction was irradiated at 300 watts, 200° C. for 20 minutes. The reaction was then reduced en vacuo and the resulting residue was isolated and purified by Gilson prep HPLC to afford 102.60 mg of N-{2-[2-(4-Morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide as a lyophilized powder. (M+H)=465.1. 1H NMR (400 MHz, DMSO, d6) δ 9.43 (s, 1H), 8.98 (s, 1H), 8.83 (s, 1H), 7.72 (d, 1H, J=7.80 Hz), 7.55 (m, 4H), 7.45 (m, 1H), 7.00 (m, 4H), 3.78 (m, 4H), 3.14 (m, 4H), 2.68 (s, 3H).

Workup

  1. customThe reaction was irradiated at 300 watts, 200° C. for 20 minutes
  2. customthe resulting residue was isolated
  3. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-63ae53cefbff475285b1a5de446dabf3
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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