2-[2-(Morpholin-4-yl)ethyl]-2H-indazol-5-amine → N-Methyl-N-(2-{2-[2-(2-morpholin-4-yl-ethyl)-2H-indazol-6-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenyl)-methanesulfonamide
Reaction equation
O[C:2]1[N:7]=[CH:6][C:5]2=[CH:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])[N:4]2[N:3]=1.[N:23]1([CH2:29][CH2:30][N:31]2[CH:39]=[C:38]3[C:33]([CH:34]=[C:35]([NH2:40])[CH:36]=[CH:37]3)=[N:32]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.N1(CCN2C=C3C(C=CC(N)=C3)=N2)CCOCC1>>[CH3:22][N:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[N:4]2[C:5]([CH:6]=[N:7][C:2]([NH:40][C:35]3[CH:36]=[CH:37][C:38]4[C:33]([CH:34]=3)=[N:32][N:31]([CH2:30][CH2:29][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:39]=4)=[N:3]2)=[CH:8][CH:9]=1)[S:18]([CH3:21])(=[O:20])=[O:19]Participants
Reactant 3
Product 1
Procedure
Following the procedure of Example 1315, N-[2-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (105 mg, 0.330 mmol) was coupled in parallel fashion to 2-(2-morpholin-4-yl-ethyl)-2H-indazol-6-ylamine (57 mg, 0.23 mmol) and 2-(2-morpholin-4-yl-ethyl)-2H-indazol-5-ylamine (57 mg, 0.23 mmol). Products were purified by RP pHPLC as described in Example 1291c. Yield of TFA salt: 51 mg (46%); LC/MS: 547 (M+H); HPLC: 97% pure, RT=2.20 min; 1H NMR: (DMSO, δ) 9.53 (s, 1H), 9.01 (s, 1H), 8.31 (d, J=7.6, 1H), 8.13 (d, J=7.9, 1H), 8.11 (s, 1H), 7.68 (d, J=7.8, 1H), 7.60 (m, 3H), 7.23 (d, J=8.9, 1H), 7.04 (d, J=4.8, 1H), 6.98 (d, J=4.8, 1H), 4.81 (t, J=5.9, 2H), 3.85 (m, 4H), 3.76 (m, 2H), 3.35 (m, 4H), 3.13 (s, 3H), 2.91 (s, 3H).
Workup
- customProducts were purified by RP pHPLC
Sources & evidence
- ORD record
- ord-0ec5b4951b2f4f168ebf3ccfdb56e5f6
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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