Diethylamine → N,N-diethyl-N'-[4-(1-ethyl-4-{2-[4-(1-pyrrolidinylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-3-yl)phenyl]urea

HRID 28901노트

반응식

HRID 28901 반응식
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[CH:19][CH:18]=4)=[CH:16][C:9]=23)[C:5]([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)=[N:4]1)[CH3:2].Cl[C:37](OC1C=CC([N+]([O-])=O)=CC=1)=[O:38].[CH2:49]([NH:51][CH2:52][CH3:53])[CH3:50]>C1COCC1>[CH2:49]([N:51]([CH2:52][CH3:53])[C:37]([NH:33][C:32]1[CH:31]=[CH:30][C:29]([C:5]2[C:6]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]4[NH:14][C:15]([C:17]5[CH:18]=[CH:19][C:20]([CH2:23][N:24]6[CH2:28][CH2:27][CH2:26][CH2:25]6)=[CH:21][CH:22]=5)=[CH:16][C:9]=34)=[CH:7][N:3]([CH2:1][CH3:2])[N:4]=2)=[CH:35][CH:34]=1)=[O:38])[CH3:50]

참가 물질

5

반응물 3

HCID 8021DiethylamineHCID 821294-Nitrophenyl chloroformateHCID 68995250HCID 68995250, 화합물

생성물 1

HCID 24816135N,N-diethyl-N'-[4-(1-ethyl-4-{2-[4-(1-pyrrolidinylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-3-yl)phenyl]urea수율 37.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cloudy mixture of 4-(1-ethyl-4-{2-[4-(1-pyrrolidinylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-3-yl)aniline (350 mg, 0.76 mmol) in dry THF (8 mL) was added 4-nitrophenyl chloroformate (168 mg, 0.83 mmol). The resultant slurry was stirred at room temperature for 45 min and diethylamine (0.32 mL, 3.03 mmol) was added. After 1 h, the reaction was concentrated under reduced pressure and diluted with 1N NaOH and EtOAc. The aqueous layer was extracted with three portions of EtOAc followed by 5% MeOH in EtOAc and the combined extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by Gilson reverse phase HPLC (MeCN/H2O with 0.1% TFA) to provide 159 mg (32%) of the title product as a bis-TFA salt (yellow solid). ESMS [M+H]+: 562.4

후처리

  1. waitAfter 1 h
  2. concentrationthe reaction was concentrated under reduced pressure
  3. additiondiluted with 1N NaOH and EtOAc
  4. extractionThe aqueous layer was extracted with three portions of EtOAc
  5. dry with materialthe combined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by Gilson reverse phase HPLC (MeCN/H2O with 0.1% TFA)

출처 및 근거

ORD 기록
ord-98387b16e1884e59af44233769455815
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419988B2

반응 노트

불러오는 중…