1-Methoxy-2-propanol → (3-Morpholin-4-yl-phenyl)-(7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine

HRID 1261978Notes

Reaction equation

HRID 1261978 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:6]2[N:5]=1)=O.C(N(CC)C(C)C)(C)C.[N:28]1([C:34]2[CH:35]=[C:36]([NH2:40])[CH:37]=[CH:38][CH:39]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.COCC(O)C>>[N:28]1([C:34]2[CH:35]=[C:36]([NH:40][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=5)[N:6]4[N:5]=3)[CH:37]=[CH:38][CH:39]=2)[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 8477683-(Morpholin-4-yl)anilineHCID 667112752-Methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711698(3-Morpholin-4-yl-phenyl)-(7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amineYield 40.7%

Procedure

2-Methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazine (125.0 mg, 0.0004839 mol), N,N-Diisopropylethylamine (0.126 mL, 0.000726 mol) and 3-Morpholin-4-yl-phenylamine (0.172 g, 0.000968 mol) were dissolved in 1-Methoxy-2-propanol (1.0 mL, 0.010 mol) and 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 en vacuo and the product was isolated and purified by Gilson prep HPLC to afford 73.26 mg of (3-Morpholin-4-yl-phenyl)-(7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine as a lyophilized powder. (M+H)=373.7. 1H NMR (400 MHz, DMSO, d6) δ 9.45 (s, 2H), 9.07 (s, 1H), 8.81 (d, 1H, J=8.00 Hz), 8.70 (d, 1H, J=3.76 Hz), 7.78 (m, 1H), 7.35 (d, 1H, J=4.76 Hz), 7.30 (s, 1H), 7.18 (m, 2H), 7.02 (d, 1H, J=4.80 Hz), 6.62 (m, 1H), 3.69 (m, 4H), 3.02 (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-f9d4f396fc994f4eacbf7ef81f35b0a1
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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