1-Methoxy-2-propanol → N-Methyl-N-{2-[2-(3-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide

HRID 1262031Notes

Reaction equation

HRID 1262031 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CS([C:17]1[N:22]=[CH:21][C:20]2=[CH:23][CH:24]=[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:32]([CH3:37])[S:33]([CH3:36])(=[O:35])=[O:34])[N:19]2[N:18]=1)=O.C(N(CC)C(C)C)(C)C.COCC(O)C>>[CH3:37][N:32]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:25]1[N:19]2[C:20]([CH:21]=[N:22][C:17]([NH:13][C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[CH:8]=3)=[N:18]2)=[CH:23][CH:24]=1)[S:33]([CH3:36])(=[O:34])=[O:35]

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 8477683-(Morpholin-4-yl)anilineHCID 54577677N-[2-(2-M ethanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide

Product 1

HCID 66711416N-Methyl-N-{2-[2-(3-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamideYield 21.6%

Procedure

3-Morpholin-4-yl-phenylamine (122.3 mg, 0.6860 mmol), N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (125.0 mg, 0.3430 mmol) and N,N-Diisopropylethylamine (0.1792 mL, 1.029 mmol) were dissolved in 1-Methoxy-2-propanol (1.25 mL, 12.8 mmol). The reaction was irradiated at 300 watts, 200° C. for 20 minutes or until HPLC showed consumption of starting material. The mixture was then reduced under nitrogen and the product was isolated and purified by Gilson prep HPLC to afford 35.51 mg of N-Methyl-N-{2-[2-(3-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide as a lyophilized powder. (M+H)=479.1. 1H NMR (400 MHz, DMSO, d6) δ 9.26 (s, 1H), 8.97 (s, 1H), 7.73 (m, 1H), 7.66 (m, 1H), 7.55 (m, 2H), 7.48 (m, 1H), 7.02 (t, 1H, J=8.09 Hz), 6.93 (d, 1H, J=4.64 Hz), 6.87 (m, 2H), 6.45 (m, 1H), 3.57 (m, 4H), 3.08 (s, 3H), 2.71 (s, 3H), 2.67 (m, 4H).

Workup

  1. customThe reaction was irradiated at 300 watts, 200° C. for 20 minutes or until HPLC
  2. customconsumption of starting material
  3. customthe product was isolated
  4. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-d5e79795a8d94600b89b86b25f1a6a9d
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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