5-Aminobenzimidazole → (3H-Benzimidazol-5-yl)-[7-(3-cyclopropylmethanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1262376

반응식

HRID 1262376 반응식
[CH:1]1([CH2:4][S:5]([C:8]2[CH:9]=[C:10]([C:14]3[N:22]4[C:17]([CH:18]=[N:19][C:20](SC)=[N:21]4)=[CH:16][CH:15]=3)[CH:11]=[CH:12][CH:13]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[N:25]1[C:29]2[CH:30]=[CH:31][C:32]([NH2:34])=[CH:33][C:28]=2[NH:27][CH:26]=1>>[N:25]1[C:29]2[CH:30]=[CH:31][C:32]([NH:34][C:20]3[N:19]=[CH:18][C:17]4=[CH:16][CH:15]=[C:14]([C:10]5[CH:11]=[CH:12][CH:13]=[C:8]([S:5]([CH2:4][CH:1]6[CH2:3][CH2:2]6)(=[O:7])=[O:6])[CH:9]=5)[N:22]4[N:21]=3)=[CH:33][C:28]=2[NH:27][CH:26]=1

참가 물질

3

반응물 2

HCID 136235-AminobenzimidazoleHCID 667121477-(3-Cyclopropylmethanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

생성물 1

HCID 66712059(3H-Benzimidazol-5-yl)-[7-(3-cyclopropylmethanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

실험 절차

Following the synthetic and purification procedures described in Example 1293d, 7-(3-cyclopropylmethanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (75 mg, 0.20 mmol) was coupled with 3H-benzimidazol-5-ylamine (45.2 mg, 0.340 mmol) at 105° C. for 86 h to afford the title compound. Yield of TFA salt: 39 mg (43%) of brown powder; LC/MS: 445 (M+H); HPLC: 97% pure, RT=2.46 min; 1H NMR: (DMSO, δ) 9.85 (s, 1H), 9.33 (s, 1H), 9.02 (s, 1H), 8.51 (s, 1H), 8.45 (d, J=7.7, 1H), 8.00 (s, 1H), 7.90 (dd, J=9.2, 1.5, 1H), 7.83 (d, J=7.7, 1H), 7.75 (m, 2H), 7.27 (d, J=4.8, 1H), 6.97 (d, J=4.8, 1H), 3.21 (d, J=7.1, 2H), 0.77 (m, 1H), 0.34 (m, 2H), 0.01 (m, 2H).

후처리

  1. custompurification procedures

출처 및 근거

ORD 기록
ord-60955aefc27d4d3995342daf0959cc61
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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