1-Methoxy-2-propanol → [7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[6-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amine

HRID 1262262Notes

Reaction equation

HRID 1262262 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.CS([C:19]1[N:24]=[CH:23][C:22]2=[CH:25][CH:26]=[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:29]=3)[N:21]2[N:20]=1)=O.C(N(CC)C(C)C)(C)C.COCC(O)C>>[CH3:37][S:34]([C:30]1[CH:29]=[C:28]([C:27]2[N:21]3[C:22]([CH:23]=[N:24][C:19]([NH:15][C:13]4[CH:12]=[CH:11][CH:10]=[C:9]([CH2:8][N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)[N:14]=4)=[N:20]3)=[CH:25][CH:26]=2)[CH:33]=[CH:32][CH:31]=1)(=[O:35])=[O:36]

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 120778076-[(4-Methylpiperazin-1-yl)methyl]pyridin-2-amineHCID 667114002-Methanesulfinyl-7-(3-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66712320[7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[6-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amine

Procedure

Into a microwave vial, 6-(4-Methyl-piperazin-1-ylmethyl)-pyridin-2-ylamine (0.149 g, 0.722 mmol), 2-Methanesulfinyl-7-(3-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (0.110 g, 0.328 mmol), N,N-Diisopropylethylamine (0.126 mL, 0.722 mmol), and 1-Methoxy-2-propanol (0.5 mL, 5 mmol) were added. The reaction was microwaved on 300 watts, 180° C. for 4 hours. The reaction mixture was purified via HPLC reverse phase chromatography with 0.1% TFA in Water and 0.1% TFA in ACN. The collected fractions were lyophilized to give [7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[6-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amine a yellow solid (20 mg, 10%). LCMS (E/I+) 478.8 (M+H). NMR 1H (DMSO-d6)-9.16 (s, 1H), 8.81 (d, 1H, J=7.82), 8.78 (s, 1H), 8.46 (dd, 1H, JJ=1.89, 5.36 Hz), 7.83-7.95 (m, 2H), 7.78 (t, 1H, J=7.57 Hz), 7.58 (d, 1H, J=5.05 Hz), 7.19 (dd, 1H, JJ=5.05, 6.94 Hz), 7.15 (d, 1H, J=5.05 Hz), 3.80 (s, 2H), 3.40-3.51 (m, 2H), 2.93-3.11 (m, 4H), 2.81 (s, 3H), 2.34-2.60 (m, 5H).

Workup

  1. customThe reaction was microwaved on 300 watts, 180° C. for 4 hours
  2. customThe reaction mixture was purified via HPLC reverse phase chromatography with 0.1% TFA in Water and 0.1% TFA in ACN

Sources & evidence

ORD record
ord-5f2b19e0330e47c698e2eadaea986137
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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