1-Methoxy-2-propanol → HCID 136355293, compound

HRID 1262275Notes

Reaction equation

HRID 1262275 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[OH:19])[N:6]2[N:5]=1)=O.[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.COCC(O)C.C(N(CC)C(C)C)(C)C>>[CH3:20][N:21]1[CH2:22][CH2:23][N:24]([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=5[OH:19])[N:6]4[N:5]=3)=[CH:29][CH:28]=2)[CH2:25][CH2:26]1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 136360288HCID 136360288, compound

Product 1

HCID 136355293HCID 136355293, compoundYield 51.7%

Procedure

Into a microwave vial, 2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenol (0.165 g, 0.604 mmol), 4-(4-Methyl-piperazin-1-yl)-phenylamine (0.254 g, 1.33 mmol), 1-Methoxy-2-propanol (1.20 mL) and N,N-Diisopropylethylamine (0.231 mL, 1.33 mmol) were added. The reaction was microwaved on 300 watts, 180° C. for 2 hours. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol). The collected fractions afforded 2-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenol as a yellow solid (125 mg, 51%). LCMS (E/I+) 401.10 (M+H). NMR 1H (DMSO-d6)-9.73 (s, 1H), 9.13 (s, 1H), 8.88 (s, 1H), 7.92 (d, 1H, J=7.74 Hz), 7.61 (d, 2H, J=8.23 Hz), 7.25 (t, 1H, J=7.26 Hz), 6.93-7.08 (m, 3H), 6.88 (d, 1H, J=4.35 Hz), 6.81 (d, 2H, J=8.23 Hz), 3.03 (bs, 4H), 2.44 (bs, 3H), 2.21 (s, 3H).

Workup

  1. customThe reaction was microwaved on 300 watts, 180° C. for 2 hours
  2. customThe solvent was removed under vacuum
  3. customThe reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol)

Sources & evidence

ORD record
ord-69ccc695c825435d86689031baf99a29
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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