2-tert-butyl-1H-benzimidazol-5-amine → [7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[1-(2-morpholin-4-yl-ethyl)-1H-indazol-5-yl]-amine

HRID 1262381Notes

Reaction equation

HRID 1262381 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15](O)=[N:16]2)=[CH:11][CH:10]=1.[N:19]1([CH2:25][CH2:26][N:27]2[C:35]3[C:30](=[CH:31][C:32]([NH2:36])=[CH:33][CH:34]=3)[CH:29]=[N:28]2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.N1(CCN2C3C(=CC=C(N)C=3)C=N2)CCOCC1.N1(CCN2C3C=CC(N)=CC=3N=C2)CCOCC1.N1(CCN2C3C=C(N)C=CC=3N=C2)CCOCC1.N1(CCN2C=C3C(C=C(N)C=C3)=N2)CCOCC1.N1(CCN2C=C3C(C=CC(N)=C3)=N2)CCOCC1.C(C1NC2C=C(N)C=CC=2N=1)(C)(C)C>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([NH:36][C:32]3[CH:31]=[C:30]4[C:35](=[CH:34][CH:33]=3)[N:27]([CH2:26][CH2:25][N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[N:28]=[CH:29]4)=[N:16]2)=[CH:11][CH:10]=1

Participants

9

Reactant 8

HCID 21134482-tert-butyl-1H-benzimidazol-5-amineHCID 226935071-(2-morpholin-4-yl-ethyl)-1H-indazol-6-ylamineHCID 574161312-[2-(Morpholin-4-yl)ethyl]-2H-indazol-5-amineHCID 574161322-[2-(Morpholin-4-yl)ethyl]-2H-indazol-6-amineHCID 574161331-[2-(Morpholin-4-yl)ethyl]-1H-benzimidazol-5-amineHCID 574161341-[2-(Morpholin-4-yl)ethyl]-1H-benzimidazol-6-amineHCID 574161351-[2-(Morpholin-4-yl)ethyl]-1H-indazol-5-amineHCID 1784892767-(2-Methoxyphenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol

Product 1

HCID 66712384[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[1-(2-morpholin-4-yl-ethyl)-1H-indazol-5-yl]-amine

Procedure

Following the procedure of Example 1315, 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (365 mg, 1.51 mmol)was coupled in parallel fashion to 1-(2-morpholin-4-yl-ethyl)-1H-indazol-5-ylamine (74 mg, 0.30 mmol), 1-(2-morpholin-4-yl-ethyl)-1H-indazol-6-ylamine (74 mg, 0.30 mmol), 1-(2-morpholin-4-yl-ethyl)-1H-benzimidazol-5-ylamine (74 mg, 0.30 mmol), 3-(2-morpholin-4-yl-ethyl)-3H-benzimidazol-5-ylamine (74 mg, 0.30 mmol), 2-(2-morpholin-4-yl-ethyl)-2H-indazol-6-ylamine (74 mg, 0.30 mmol), 2-(2-morpholin-4-yl-ethyl)-2H-indazol-5-ylamine (74 g, 30 mmol) and 2-tert-butyl-3H-benzimidazol-5-ylamine (57 mg, 0.30 mmol). Products were purified by RP pHPLC as described in Example 1291c. Yield of TFA salt: 103 mg (82%); LC/MS: 470 (M+H); HPLC: 97% pure, RT=2.51 min; 1H NMR: (DMSO, δ) 9.86 (s, 1H), 9.50 (s, 1H), 8.97 (s, 1H), 8.36 (s, 1H), 7.83 (d, J=7.5, 1H), 7.62 (m, 2H), 7.54 (t, J=7.7, 1H), 7.32 (d, J=8.3, 1H), 7.18 (t, J=7.5, 1H), 6.95 (d, J=4.8, 1H), 6.93 (d, J=4.8, 1H), 4.79 (t, J=6.3, 2H), 3.95 (m, 2H), 3.81 (s, 3H), 3.71 (m, 6H), 3.16 (m, 2H).

Workup

  1. customProducts were purified by RP pHPLC

Sources & evidence

ORD record
ord-49d94f4639c84a7a9793a56b00ebb0fa
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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