Methanesulfonic Acid → 5-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-indol-2-one

HRID 1262035Notes

Reaction equation

HRID 1262035 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[O:19][CH3:20])[N:6]2[N:5]=1)=O.CS(O)(=O)=O.[NH2:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])[CH2:30]2.COCC(O)C>>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:6]2[C:7]([CH:8]=[N:9][C:4]([NH:26][C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[NH:32][C:31](=[O:36])[CH2:30]4)=[N:5]2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6395Methanesulfonic AcidHCID 79001-Methoxy-2-propanolHCID 27732135-Amino-2-oxindoleHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667111645-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-indol-2-oneYield 5.6%

Procedure

2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (75.0 mg, 0.000261 mol), Methanesulfonic acid (0.03388 mL, 0.0005220 mol) and [B] 5-Amino-1,3-dihydro-indol-2-one (77.3 mg, 0.000522 mol) were dissolved in 1-Methoxy-2-propanol (0.74 mL, 0.0076 mol) and the reaction was irradiated at 300 watts, 200° C. for 40 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 5.40 mg of 5-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-indol-2-one as a lyophilized powder. (M+H)=371.9. 1H NMR (400 MHz, DMSO, d6) δ 10.19 (s, 1H), 9.25 (s, 1H), 8.91 (s, 1H), 7.78 (d, 1H, J=7.53 Hz), 7.74 (s, 1H), 7.47 (t, 1H, J=7.53 Hz), 7.39 (d, 1H, J=7.88 Hz), 7.23 (d, 1H, J=8.09 Hz), 7.13 (t, 1H, J=7.28 Hz), 6.90 (dd, 2H, J=4.61, 6.41 Hz), 6.64 (d, 1H, J=8.37 Hz), 3.78 (s, 3H), 3.38 (s, 2H).

Workup

  1. customthe reaction was irradiated at 300 watts, 200° C. for 40 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-a74d0d64bca746469bd974d04a36da74
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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