Diisopropylethylamine → Tert-butyl 4-(6-((3-fluoro-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methylcarbamoyl)pyridin-3-yl)piperazine-1-carboxylate

HRID 711258노트

반응식

HRID 711258 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20](O)=[O:21])=[N:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:23][C:24]1[C:25]([C:32]2[CH:37]=[CH:36][N:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)=[N:26][CH:27]=[C:28]([CH2:30][NH2:31])[CH:29]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[F:23][C:24]1[C:25]([C:32]2[CH:37]=[CH:36][N:35]=[C:34]([C:38]([F:41])([F:39])[F:40])[CH:33]=2)=[N:26][CH:27]=[C:28]([CH2:30][NH:31][C:20]([C:17]2[N:18]=[CH:19][C:14]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]3)=[CH:15][CH:16]=2)=[O:21])[CH:29]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67208645(3-Fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methanamineHCID 729428105-(4-(tert-Butoxycarbonyl)piperazin-1-yl)picolinic acid

생성물 1

HCID 68079197Tert-butyl 4-(6-((3-fluoro-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methylcarbamoyl)pyridin-3-yl)piperazine-1-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 5-(4-(tert-butoxycarbonyl)piperazin-1-yl)picolinic acid 49-4 (92 mg, 0.3 mmol), (3-fluoro-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 84-2 (81 mg, 0.3 mmol) and HATU (114 mg, 0.3 mmol) in DMF (1.5 mL) was added DIEA (0.15 mL, 0.9 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (100 mL), washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, and eluted with 5% methanol in dichloromethane to give tert-butyl 4-(6-((3-fluoro-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methylcarbamoyl)pyridin-3-yl)piperazine-1-carboxylate 49-5 as a pale yellow oil. MS m/z 561.2 (M+1)

후처리

  1. washwashed with H2O and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness by rotary evaporation
  4. customThe crude product was purified by silica gel flash chromatography
  5. washeluted with 5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-e0e9058fc269408594d9e1895b21f5a9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181235B2

반응 노트

불러오는 중…