1-Methoxy-2-propanol → {4-[3-(4-Methyl-piperazin-1-yl)-propoxy]-phenyl}-(7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine

HRID 1261912Notes

Reaction equation

HRID 1261912 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.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:22][CH2:21]1.COCC(O)C.C(N(CC)C(C)C)(C)C>>[CH3:19][N:20]1[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][O:29][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:14]=[N:15][CH:16]=[CH:17][CH:18]=5)[N:6]4[N:5]=3)=[CH:34][CH:35]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 221246044-[3-(4-Methylpiperazin-1-yl)propoxy]anilineHCID 667112752-Methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711162{4-[3-(4-Methyl-piperazin-1-yl)-propoxy]-phenyl}-(7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine

Procedure

Into a Microwave vial, 2-Methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazine (0.104 g, 0.000404 mol), 4-[3-(4-Methyl-piperazin-1-yl)-propoxy]-phenylamine (0.221 g, 0.000888 mol), 1-Methoxy-2-propanol (0.971 mL, 0.00993 mol) and N,N-Diisopropylethylamine (0.155 mL, 0.000888 mol) were added. The reaction was microwaved on 300 watts, 170° C. for 50 minutes. The solvent was removed under vacuum. The desired product was isolated via ISCO column chromatography with DCM and methanol as eluant (0 to 15% methanol). The collected fractions afforded {4-[3-(4-Methyl-piperazin-1-yl)-propoxy]-phenyl}-(7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine as a yellow solid (25 mg, 14%). MP 135-139° C. LCMS (E/I+) 444.8 (M+H). NMR 1H (DSMO-d6)-9.38-9.46 (m, 2H), 9.03 (s, 1H), 8.66 (d, 1H, J=8.08 Hz), 8.61 (d, 1H, J=4.67 Hz), 7.60-7.70 (m, 3H), 7.32 (d, 1H, J=4.81 Hz), 6.98 (d, 1H, J=4.80 Hz), 6.93 (d, 2H, J=9.00 Hz), 4.03 (t, 2H, J=5.26 Hz), 2.30-3.60 (m, 13H), 1.95-2.10 (bm, 2H).

Workup

  1. customThe reaction was microwaved on 300 watts, 170° C. for 50 minutes
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2203d214ef3044b78cfd5200b86feaa2
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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