Methanesulfonic Acid → HCID 66711001, compound
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[N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[N:6]2[N:5]=1)=O.CS(O)(=O)=O.[CH3:30][O:31][C:32]1[CH:40]=[C:39]2[C:35]([CH2:36][N:37]([CH3:41])[CH2:38]2)=[CH:34][C:33]=1[NH2:42]>COCC(O)C>[CH3:30][O:31][C:32]1[CH:40]=[C:39]2[C:35]([CH2:36][N:37]([CH3:41])[CH2:38]2)=[CH:34][C:33]=1[NH:42][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[N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[N:6]2[N:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 135 °C
Procedure
N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (90.00 mg, 0.247), methanesulfonic acid (0.048 mL, 0.74 mmol) and 6-methoxy-2-methyl-2,3-dihydro-1H-isoindol-5-ylamine (88.03 mg, 0.494 mmol) were combined in 1-methoxy-2-propanol (1.45 mL) in a capped tube and the reaction was stirred at 135° C. for 24 h. The product was isolated by reverse phase hplc and neutralization to the free amine to afford N-{2-[2-(6-methoxy-2-methyl-2,3-dihydro-1H-isoindol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide as a brown amorphous solid (5 mg, 4%). 1H-NMR (CDCl3) δ 8.72 (s, 1H), 8.02 (s, 1H), 7.90 (m, 1H), 7.52 (m, 4H), 7.03 (d, J=4.5 Hz, 1H), 6.86 (d, J=4.5 Hz, 1H), 6.72 (s, 1H), 3.89 (m, 2H), 3.88 (s, 3H), 3.74 (m, 2H), 3.11 (s, 3H), 2.67 (s, 3H), 2.60 (s, 3H); LC/MS (ESI+): 479.1 (M+H).
Sources & evidence
- ORD record
- ord-3e58d7430be34673999723d8e0d4d87f
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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