Dimethylformamide → tert-Butyl((1R)-4-(2-(6-isoquinolinylcarbonyl)hydrazino)-4-oxo-1-(4-(trifluoromethyl)benzyl)butyl)carbamate

HRID 598901노트

반응식

HRID 598901 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.CN(C(O[N:22]1[N:30]=NC2C=CC=N[C:23]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:38]([O:42][C:43](=[O:61])[NH:44][C@@H:45]([CH2:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][CH:52]=1)[CH2:46][CH2:47]NN)([CH3:41])([CH3:40])[CH3:39].CN(C=[O:66])C>>[C:38]([O:42][C:43](=[O:61])[NH:44][C@@H:45]([CH2:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]([F:59])([F:58])[F:60])=[CH:53][CH:52]=1)[CH2:46][CH2:47][C:23]([NH:22][NH:30][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH:1]=[N:2][CH:3]=[CH:4]2)=[O:13])=[O:66])([CH3:40])([CH3:39])[CH3:41]

참가 물질

5

반응물 4

HCID 6228Dimethylformamide3회HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22128831Isoquinoline-6-carboxylic acidHCID 57950716tert-butyl((1S)-3-hydrazino-1-(4-(trifluoromethyl)benzyl)propyl)carbamate

생성물 1

HCID 57950611tert-Butyl((1R)-4-(2-(6-isoquinolinylcarbonyl)hydrazino)-4-oxo-1-(4-(trifluoromethyl)benzyl)butyl)carbamate수율 71%

실험 절차

Isoquinoline-6-carboxylic acid (0.22 g, 1.3 mmol) (commercially available from AstaTech Product List (Order Number 62874)) and HATU (0.50 g, 1.3 mmol) were mixed in 10 mL DMF along with 0.21 mL DEA. The mixture was stirred at room temperature for 15 minutes. The mixture was added dropwise to a DMF solution of tert-butyl((1S)-3-hydrazino-1-(4-(trifluoromethyl)benzyl)propyl)carbamate (0.45 g, 1.2 mmol) and 0.21 mL of DEA in 10 mL DMF. The resulting mixture was stirred at room temperature for 1 hour. After the solvent was removed, the residue was dissolved in EtOAc and saturated aqueous sodium bicarbonate, and dried over sodium sulfate. The solvent was evaporated and the residue was triturated with DCM to provide the product as an off-white solid (0.45 g, 71%). LCMS (API-ES) m/z: 531 (M+H+).

후처리

  1. stirringThe resulting mixture was stirred at room temperature for 1 hour
  2. customAfter the solvent was removed
  3. dissolutionthe residue was dissolved in EtOAc
  4. dry with materialsaturated aqueous sodium bicarbonate, and dried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was triturated with DCM

출처 및 근거

ORD 기록
ord-0c1106f0bd6a4efa812ad90310ec4466
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

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