Triethylamine → 2-[3,5-Bis(trifluoromethyl)phenyl]-n{4-(4-fluoro-2-methylphenyl)-6-[(7as)-3-oxotetrahydro-1h-pyrrolo[1,2-c]imidazol-2(3h)-yl]-3-pyridinyl}-n,2-dimethylpropanamide

HRID 2245493노트

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HRID 2245493 반응식
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C:13]([CH3:40])([CH3:39])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([NH:32][CH2:33][C@@H:34]3[CH2:38][CH2:37][CH2:36][NH:35]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.Cl[C:51](Cl)([O:53]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:40])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[CH2:33][C@@H:34]4[CH2:38][CH2:37][CH2:36][N:35]4[C:51]3=[O:53])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 592157702-[3,5-bis(trifluoromethyl)phenyl]-N-(4-(4-fluoro-2-methylphenyl)-6-{[(2S)-2-pyrrolidinylmethyl]amino}-3-pyridinyl)-N,2-dimethylpropanamide

생성물 1

HCID 160639992-[3,5-Bis(trifluoromethyl)phenyl]-n{4-(4-fluoro-2-methylphenyl)-6-[(7as)-3-oxotetrahydro-1h-pyrrolo[1,2-c]imidazol-2(3h)-yl]-3-pyridinyl}-n,2-dimethylpropanamide수율 37.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

The starting 2-[3,5-bis(trifluoromethyl)phenyl]-N-(4-(4-fluoro-2-methylphenyl)-6-{[(2S)-2-pyrrolidinylmethyl]amino}-3-pyridinyl)-N,2-dimethylpropanamide (D62, 38 mg, 0.064 mmol) was dissolved in 1 mL of anhydrous dichloromethane and treated with triethylamine (20 μL, 0.143 mmol). The solution was brought to 0° C. and triphosgene (10 mg, 0.034 mmol) was added. The reaction was stirred at 0° C. for 15 min, then brought to room temperature. After 24 h, the reaction was diluted with dichloromethane (10 mL) and extracted with brine. The organics were collected and the solvent removed. The product was isolated by flash chromatography (silica, cyclohexane: EtOAc 80:20 to EtOAc). Thus were obtained 8 mg of the target compound.

후처리

  1. customwas brought to 0° C.
  2. custombrought to room temperature
  3. waitAfter 24 h
  4. extractionextracted with brine
  5. customThe organics were collected
  6. customthe solvent removed
  7. customThe product was isolated by flash chromatography (silica, cyclohexane: EtOAc 80:20 to EtOAc)

출처 및 근거

ORD 기록
ord-71a0aa2ad34f46f2acf1df488f2cadf0
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683056B2

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