Triethylamine → HCID 44200596、化合物

HRID 2400378ノート

反応式

HRID 2400378 の反応式
[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

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 821294-Nitrophenyl chloroformateHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 68781893HCID 68781893、化合物

生成物 1

HCID 44200596HCID 44200596、化合物

試薬・触媒・溶媒 1

HCID 10340Sodium Carbonate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-ddd8d990a9c34ce182487dd7fea32861
出典データセット
uspto-grants-2014_08
特許番号
US08796260B2

反応ノート

読み込み中…