Triethylamine → HCID 44200596, 화합물

HRID 2400378노트

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HRID 2400378 반응식
[Cl:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][N:12]3[C:19]([C:20]4([C:23]([F:26])([F:25])[F:24])[CH2:22][CH2:21]4)=[CH:18][N:17]=[C:13]3[C@H:14]([NH2:16])[CH2:15][C:4]=2[CH:3]=1.C(N(CC)CC)C.Cl[C:35](OC1C=CC([N+]([O-])=O)=CC=1)=[O:36].Cl.Cl.[NH:49]1[CH2:54][CH2:53][CH:52]([N:55]2[C:63]3[C:58](=[N:59][CH:60]=[CH:61][CH:62]=3)[NH:57][C:56]2=[O:64])[CH2:51][CH2:50]1>C(=O)([O-])[O-].[Na+].[Na+]>[Cl:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][N:12]3[C:19]([C:20]4([C:23]([F:24])([F:25])[F:26])[CH2:21][CH2:22]4)=[CH:18][N:17]=[C:13]3[C@H:14]([NH:16][C:35]([N:49]3[CH2:50][CH2:51][CH:52]([N:55]4[C:63]5[C:58](=[N:59][CH:60]=[CH:61][CH:62]=5)[NH:57][C:56]4=[O:64])[CH2:53][CH2:54]3)=[O:36])[CH2:15][C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 821294-Nitrophenyl chloroformateHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 68781893HCID 68781893, 화합물

생성물 1

HCID 44200596HCID 44200596, 화합물

시약·촉매·용매 1

HCID 10340Sodium Carbonate용매

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온도
0 °C

실험 절차

To solution of (7R)-4-chloro-10-[1-(trifluoromethyl)cyclopropyl]-3,6,7,12-tetrahydroimidazo[1′,2′:1,7]azepino[3,4-e]indazol-7-amine (100 mg, 0.3 mmol) and triethyl amine (120 uL, 0.9 mmole) is added 4-nitrophenyl chloroformate (60 mg, 0.3 mmol) and stirred at 0° C. for 1 hr. 1-Piperidin-4-yl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one dihydrochloride [Burgey et al. WO 2006/044504], (87 mg, 0.3 mmol), is added along with triethylamine (120 uL, 0.9 mmol) and the reaction mixture is stirred at ambient temperature for 18 h. Saturated aqueous sodium carbonate (50 mL) is added and the mixture is extracted with dichloromethane (3×25 mL) The combined organic layers are washed with saturated aqueous sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane→93% dichloromethane/methanol] provides the title compound.

후처리

  1. stirringthe reaction mixture is stirred at ambient temperature for 18 h
  2. extractionthe mixture is extracted with dichloromethane (3×25 mL) The combined organic layers
  3. washare washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography [100% dichloromethane→93% dichloromethane/methanol]

출처 및 근거

ORD 기록
ord-ddd8d990a9c34ce182487dd7fea32861
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796260B2

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