Diisopropylethylamine → 1-(t-butylamino)-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)isoquinoline-5-carboxamide

HRID 1051250노트

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HRID 1051250 반응식
[C:1]([NH:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([OH:18])=O)[C:10]=2[CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].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.[NH2:52][C:53]1[CH:54]=[C:55]([NH:60][C:61](=[O:72])[C:62]2[CH:67]=[CH:66][CH:65]=[C:64]([C:68]([F:71])([F:70])[F:69])[CH:63]=2)[CH:56]=[CH:57][C:58]=1[CH3:59]>CN(C)C=O.C(OCC)(=O)C>[C:1]([NH:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([NH:52][C:53]3[CH:54]=[C:55]([NH:60][C:61](=[O:72])[C:62]4[CH:67]=[CH:66][CH:65]=[C:64]([C:68]([F:69])([F:70])[F:71])[CH:63]=4)[CH:56]=[CH:57][C:58]=3[CH3:59])=[O:18])[C:10]=2[CH:9]=[CH:8][N:7]=1)([CH3:2])([CH3:3])[CH3:4]

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 11529455N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamideHCID 825711051-(t-Butylamino)isoquinoline-5-carboxylic acid

생성물 1

HCID 1180908921-(t-butylamino)-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)isoquinoline-5-carboxamide수율 18.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

1-(t-Butylamino)isoquinoline-5-carboxylic acid (0.33 g, 1.35 mmol) obtained in Step (6) of Preparation Example 1 was dissolved in dimethyl formamide (3 mL), added with HATU (0.62 g, 1.62 mmol) and DIPEA (0.47 mL, 2.70 mmol), and stirred for 10 minutes. The reaction mixture was added with N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide (0.40 g, 1.35 mmol) obtained in Step (2) above, and stirred for 12 hours or more at room temperature. The reaction mixture was diluted with ethyl acetate, and washed with a saturated sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography to obtain the title compound (0.13 g, 18%).

후처리

  1. stirringstirred for 12 hours or more at room temperature
  2. washwashed with a saturated sodium bicarbonate solution and saline
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrated compound was purified

출처 및 근거

ORD 기록
ord-8e361e2ec76647039aaa5d59e86b7a8e
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388165B2

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