Dimethyl Sulfoxide → HCID 66711518, compound

HRID 1262087Notes

Reaction equation

HRID 1262087 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[O:15]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([C:25]3[N:33]4[C:28]([CH:29]=[N:30][C:31](S(C)=O)=[N:32]4)=[CH:27][CH:26]=3)[C:19]=2[O:18][CH2:17][CH2:16]1.C([O-])(=O)C.[K+].CS(C)=O>>[O:15]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([C:25]3[N:33]4[C:28]([CH:29]=[N:30][C:31]([NH:14][C:11]5[CH:12]=[CH:13][C:8]([N:5]6[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]6)=[CH:9][CH:10]=5)=[N:32]4)=[CH:27][CH:26]=3)[C:19]=2[O:18][CH2:17][CH2:16]1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 517044Potassium AcetateHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 66710900HCID 66710900, compound

Product 1

HCID 66711518HCID 66711518, compoundYield 64.4%

Conditions

Temperature
140 °C

Procedure

A mixture of 4-(4-Methyl-piperazin-1-yl)-phenylamine (0.086 g, 0.45 mmol), 7-(2,3-Dihydro-1,4-benzodioxin-5-yl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (0.08 g, 0.20 mmol) and Potassium acetate (0.12 g, 1.2 mmol) in Dimethyl sulfoxide (0.9 mL, 10 mmol) was heated in sealed tube at 140° C. for 4 hours. Dilution of the mixture with water (20 mL) and extraction with DCM, gave a brown solid. Purification by prep plate chromatography with DCM-methanol (10-1) gave [7-(2,3-Dihydro-1,4-benzodioxin-5-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (0.057 g, 50%). MP: 212-213° C.; LCMS (m/e) 443 (M+1); 1H-NMR (DMSO-d6, 400 MHz) δ 9.16 (s, 1H), 8.91 (s, 1H), 7.60-7.58 (d, 2H, J=9.00 Hz), 7.44-7.42 (dd, 1H, J=4.97 Hz), 7.02-6.96 (q, 2H, J=8.04 Hz), 6.93-6.92 (d, 1H, J=4.65 Hz), 6.88-6.87 (d, 1H, J=4.64 Hz), 6.81-6.79 (d, 2H, J=9.01 Hz), 5.76 (s, 1H), 4.30-4.25 (d, 4H, J=4.88 Hz), 3.32 (s, 3H), 3.03 (s, 3H), 2.45-2.43 (t, 1H, J=4.76 Hz), 2.21 (s, 1H).

Workup

  1. extractionDilution of the mixture with water (20 mL) and extraction with DCM
  2. customgave a brown solid
  3. customPurification by prep plate chromatography with DCM-methanol (10-1)

Sources & evidence

ORD record
ord-4ff364824a6341fd979f48c81fccdc31
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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