1-Methoxy-2-propanol → HCID 66712711, compound

HRID 1262321Notes

Reaction equation

HRID 1262321 reaction equation
[CH3:1][S:2]([N:5]([CH3:29])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:20]2[C:15]([CH:16]=[N:17][C:18](OS(C(F)(F)F)(=O)=O)=[N:19]2)=[CH:14][CH:13]=1)(=[O:4])=[O:3].C(N(CC)C(C)C)(C)C.COC1C=C([CH2:47][N:48]2[CH2:53][CH2:52][N:51](C)[CH2:50][CH2:49]2)C=CC=1N.COCC(O)C>>[CH3:29][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:20]2[C:15]([CH:16]=[N:17][C:18]([N:51]3[CH2:52][CH2:53][N:48]([CH3:47])[CH2:49][CH2:50]3)=[N:19]2)=[CH:14][CH:13]=1)[S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 574161102-Methoxy-4-[(4-methylpiperazin-1-yl)methyl]anilineHCID 86661681Trifluoro-methanesulfonic acid 7-[2-(methanesulfonyl-methyl-amino)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 66712711HCID 66712711, compound

Conditions

Temperature
120 °C

Procedure

Into a 8-dram vial, Trifluoro-methanesulfonic acid 7-[2-(methanesulfonyl-methyl-amino)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (89 mg, 0.20 mmol), N,N-Diisopropylethylamine (0.0757 mL, 0.435 mmol), 2-Methoxy-4-(4-methyl-piperazin-1-ylmethyl)-phenylamine (100 mg, 0.4 mmol) and 1-Methoxy-2-propanol (0.71 mL) were added. The reaction mixture was heated at 120° C. for 6 hours. The solvent was removed under vacuum. 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 N-Methyl-N-{2-[2-(4-methyl-piperazin-1-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide as a yellow solid. LCMS (E/I+) 401.20 (M+H). NMR 1H (DMSO-d6)-9.90 (bs, 1H), 8.99 (s, 1H), 7.88 (d, 1H, J=7.02 Hz), 7.65 (d, 1H, J=7.48 Hz), 7.45-7.54 (m, 2H), 7.00 (d, 1H, J=4.70 Hz), 6.92 (d, 1H, J=4.70 Hz), 4.45 (d, 2H, J=12.95 Hz), 3.49 (d, 2H, J=11.09 Hz), 3.03-3.25 (m, 7H), 2.89 (s, 3H), 2.82 (s, 3H).

Workup

  1. customThe solvent was removed under vacuum
  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-79edcc38da3d4db3b2a0524df8d7b326
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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