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 658021노트

반응식

HRID 658021 반응식
[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]

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-ac8981b43f524291aedbd489867b120c
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076336B2

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