Water → N-[(cyclohexylamino)propyl]-4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzamide

HRID 1875471

반응식

HRID 1875471 반응식
[O:1]=[C:2]1[C:6]2[N:7]=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[NH:4][N:3]1[C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.[CH:33]1([NH:39][CH2:40][CH2:41][CH2:42][NH2:43])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.O>CC(N(C)C)=O>[CH:33]1([NH:39][CH2:40][CH2:41][CH2:42][NH:43][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:15]([N:3]3[C:2](=[O:1])[C:6]4[N:7]=[N:8][C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=5[C:5]=4[NH:4]3)=[CH:16][CH:17]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

참가 물질

6

반응물 4

HCID 962WaterHCID 18718N-Cyclohexyl-1,3-propanediamineHCID 81531DiisopropylethylamineHCID 589748734-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

생성물 1

HCID 58974890N-[(cyclohexylamino)propyl]-4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzamide수율 62%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride (97 mg, 0.30 mmol) was dissolved in anhydrous DMA (2 ml). Diisopropylethylamine (39 mg, 53 μl, 0.60 mmol) was added followed by N-cyclohexyl-1,3-propanediamine (52 mg, 0.60 mmol). The mixture was stirred for 30 min. Water (5 ml) was added to give a dark red suspension. The mixture was extracted with n-butanol (2×20 ml). The combined organic phases were washed with water and concentrated under vacuum until precipitation was observed. Hexane (20 ml) and ethyl acetate (10 ml) were added, the solids were collected by filtration and dried under vacuum. The product was isolated as a dark red powder (82 mg, 0.18 mmol, 62%). LCMS: m/z 445 [M+H]+.

후처리

  1. customto give a dark red suspension
  2. extractionThe mixture was extracted with n-butanol (2×20 ml)
  3. washThe combined organic phases were washed with water
  4. concentrationconcentrated under vacuum until precipitation
  5. additionHexane (20 ml) and ethyl acetate (10 ml) were added
  6. filtrationthe solids were collected by filtration
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-08582a8bf0c5430d9b4d907a790ed07e
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309552B2

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