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

HRID 1262028Notes

Reaction equation

HRID 1262028 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CS([C:19]1[N:24]=[CH:23][C:22]2=[CH:25][CH:26]=[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[N:34]([CH3:39])[S:35]([CH3:38])(=[O:37])=[O:36])[N:21]2[N:20]=1)=O.C(N(CC)C(C)C)(C)C.COCC(O)C>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:19]2[N:24]=[CH:23][C:22]3=[CH:25][CH:26]=[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[N:34]([CH3:39])[S:35]([CH3:38])(=[O:37])=[O:36])[N:21]3[N:20]=2)=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 176047884-Methoxy-3-morpholin-4-yl-phenylamineHCID 54577677N-[2-(2-M ethanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide

Product 1

HCID 66712227N-{2-[2-(4-Methoxy-3-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamideYield 38.7%

Procedure

4-Methoxy-3-morpholin-4-yl-phenylamine (80.0 mg, 0.384 mmol), N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (70.0 mg, 0.192 mmol) and N,N-Diisopropylethylamine (0.100 mL, 0.576 mmol) were dissolved in 1-Methoxy-2-propanol (0.75 mL, 7.7 mmol). The reaction was irradiated at 300 watts, 200° C. for 20 minutes or until HPLC showed consumption of starting material. The reaction mixture was then reduced and the crude residue was isolated and purified by Gilson prep HPLC to afford 37.80 mg of N-{2-[2-(4-Methoxy-3-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide as a lyophilized powder. (M+H)=509.0. 1H NMR (400 MHz, DMSO, d6) δ 9.18 (s, 1H), 8.94 (s, 1H), 7.73 (m, 1H), 7.65 (m, 1H), 7.52 (m, 2H), 7.41 (m, 1H), 7.05 (d, 1H, J=8.80 Hz), 6.91 (m, 1H), 6.83 (m, 2H), 3.72 (s, 3H), 3.61 (m, 4H), 3.06 (s, 3H), 2.79 (s, 3H), 2.60 (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 crude residue was isolated
  4. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-3d6df35bb87440bd97182d752f35fa65
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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