1-Methyl-1H-benzimidazol-6-amine → N-{2-[2-(3-Methyl-3H-benzoimidazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide

HRID 1262372

반응식

HRID 1262372 반응식
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[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[N:6]2[N:5]=1)=O.[CH3:24][N:25]1[C:29]2[CH:30]=[C:31]([NH2:34])[CH:32]=[CH:33][C:28]=2[N:27]=[CH:26]1>>[CH3:24][N:25]1[C:29]2[CH:30]=[C:31]([NH:34][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=5[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[N:6]4[N:5]=3)[CH:32]=[CH:33][C:28]=2[N:27]=[CH:26]1

참가 물질

3

반응물 2

HCID 136802831-Methyl-1H-benzimidazol-6-amineHCID 66711409N-[2-(2-methylsulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide

생성물 1

HCID 66711756N-{2-[2-(3-Methyl-3H-benzoimidazol-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide

실험 절차

Following the synthetic and purification procedures described in Example 1293d, N-[2-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide (56 mg, 0.16 mmol) was coupled with 3-methyl-3H-benzimidazol-5-ylamine (40 mg, 0.28 mmol) at 105° C. for 86 h to afford the title compound. Yield of TFA salt: 19 mg (22%) of brown powder; LC/MS: 434 (M+H); HPLC: 95% pure, RT=2.19 min; 1H NMR: (DMSO, δ) 10.01 (s, 1H), 9.92 (s, 1H), 9.33 (s, 1H), 9.08 (s, 1H), 8.40 (s, 1H), 7.93 (d, J=7.7, 1H), 7.80 (m, 1H), 7.77 (d, J=9.0, 1H), 7.71 (d, J=9.0, 1H), 7.55 (t, J=7.8, 1H), 7.29 (d, J=7.9, 1H), 7.09 (d, J=4.8, 1H), 7.03 (d, J=4.8, 1H), 3.84 (s, 3H), 3.01 (s, 3H).

후처리

  1. custompurification procedures

출처 및 근거

ORD 기록
ord-2371c9cf07f34460a88040a09d8cb3f3
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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