Hydrochloric Acid → 1-(3-tert-Butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclopropylmethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone hydrochloride

HRID 658021ノート

反応式

HRID 658021 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([C:12]([NH2:15])=[N:13][N:14]=3)[N:11]=2)[CH2:3][CH2:2]1.Br[CH2:17][C:18]([C:20]1[CH:25]=[C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:23]([O:32][CH3:33])=[C:22]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:21]=1)=[O:19].[ClH:38]>CN(C=O)C>[ClH:38].[C:34]([C:22]1[CH:21]=[C:20]([C:18](=[O:19])[CH2:17][N:13]2[C:12](=[NH:15])[N:10]3[N:11]=[C:6]([O:5][CH2:4][CH:1]4[CH2:2][CH2:3]4)[CH:7]=[CH:8][C:9]3=[N:14]2)[CH:25]=[C:24]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[C:23]=1[O:32][CH3:33])([CH3:37])([CH3:35])[CH3:36]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 229297822-Bromo-1-(3-tert-butyl-4-methoxy-5-morpholinophenyl)ethanoneHCID 581369646-Cyclopropylmethoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

生成物 1

HCID 669416281-(3-tert-Butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclopropylmethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone hydrochloride

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

6-Cyclopropylmethoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W1.009; 350 mg) was initially charged in DMF (5 ml) at RT while stirring, and 2-bromo-1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)ethanone (O1.003; 631 mg) predissolved in DMF (5 ml) was added dropwise. The reaction mixture was stirred at RT for 14 h. Then the solvent was removed under reduced pressure and the residue was purified using silica gel (40 g cartridge, dichloromethane/ethanol gradient of 0-40% in 60 min). The product was taken up with a little acetonitrile, diluted with water and, after addition of 2 eq. of HCl, freeze-dried. 500 mg of the title compound were obtained. LC-MS rt: 1.37 min [M+H]+: 495.2 (met. a)

後処理

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred at RT for 14 h
  3. customThen the solvent was removed under reduced pressure
  4. customthe residue was purified
  5. customsilica gel (40 g cartridge, dichloromethane/ethanol gradient of 0-40% in 60 min)
  6. additiondiluted with water
  7. customfreeze-dried

出典と根拠

ORDレコード
ord-ac8981b43f524291aedbd489867b120c
出典データセット
uspto-grants-2011_12
特許番号
US08076336B2

反応ノート

読み込み中…