2-(4-{4-[7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-trifluoromethyl-phenyl}-3,6-dihydro-2H pyridin-1-yl) acetamide → Trifluoroacetic acid

HRID 1262155노트

반응식

HRID 1262155 반응식
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH2:28][CH2:29][N:30]([CH2:33][C:34]([NH2:36])=[O:35])[CH2:31][CH:32]=5)=[C:23]([C:37]([F:40])([F:39])[F:38])[CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].CS(C1C=C(C2N3C(C=N[C:57]([OH:60])=N3)=CC=2)C=CC=1)(=O)=O.NC1C=CC(C2CCN(CC(N)=O)CC=2)=C([C:78]([F:81])([F:80])[F:79])C=1>CS(C)=O>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH2:28][CH2:29][N:30]([CH2:33][C:34]([NH2:36])=[O:35])[CH2:31][CH:32]=5)=[C:23]([C:37]([F:39])([F:38])[F:40])[CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4].[C:57]([OH:60])([C:78]([F:81])([F:80])[F:79])=[O:3]

참가 물질

6

반응물 3

HCID 667116422-(4-{4-[7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-trifluoromethyl-phenyl}-3,6-dihydro-2H pyridin-1-yl) acetamideHCID 667118982-[4-(4-Amino-2-trifluoromethyl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetamideHCID 178504720HCID 178504720, 화합물

생성물 2

HCID 6422Trifluoroacetic acid수율 72%HCID 667116422-(4-{4-[7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-trifluoromethyl-phenyl}-3,6-dihydro-2H pyridin-1-yl) acetamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

2-(4-{4-[7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-trifluoromethyl-phenyl}-3,6-dihydro-2H pyridin-1-yl) acetamide. 7-(3-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (46.1 mg, 0.159 mmol) and 2-[4-(4-Amino-2-trifluoromethyl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetamide (0.0596 g, 0.199 mmol) were reacted in an analogous manner to Example 908D at 50° C. for 16 h. Concentrated reaction mixture, took up in DMSO, and purified by Gilson RP-HPLC. The fractions containing desired product were lyophilized to afford title compound as a TFA salt (65 mg, 72%). LCMS=570.9 (M+H), HPLC rt=2.435, purity=95% , 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 10.14 (bs, 1H), 9.60 (s, 1H), 9.11 (s, 1H), 8.56 (s, 1H), 8.49 (d J=7.8 Hz, 1H), 8.11 (d, J=8.8 Hz, 1H), 8.01 (s, 2H), 7.95 (d, J=7.9 Hz, 1H) 7.80-7.73 (m, 2H), 7.36-7.34 (m, 2H), 7.07 (d, J=4.7 Hz, 1H), 5.60 (s, 1H), 4.02 (s, 2H), 4.01-3.95 (m, 1H), 3.90-3.80 (m, 1H), 3.65-3.55 (m, 1H), 3.44-3.34 (m, 1H), 3.20 (s, 3H), 2.82-2.70 (m, 1H), 2.45-2.38 (m, 1H).

후처리

  1. concentrationConcentrated
  2. customreaction mixture
  3. custompurified by Gilson RP-HPLC
  4. additionThe fractions containing desired product

출처 및 근거

ORD 기록
ord-f53b4b8814a5461aa5dd77f9aea3926b
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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