p-Chlorophenyl dichlorophosphate → HCID 10029911, 화합물

HRID 2222231

반응식

HRID 2222231 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH2:12][N:13]1[C:21]([C:22]2[N:26]([CH3:27])[CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)=[C:20]2[C:15]([N:16]([CH2:32][CH:33]3[CH2:35][CH2:34]3)[C:17](=[O:31])[NH:18][C:19]2=O)=[N:14]1.P(Cl)(Cl)(=O)[O:37][C:38]1[CH:43]=CC(Cl)=CC=1.[N+:48](C1N=CNN=1)([O-])=O>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH2:12][N:13]1[C:21]([C:22]2[N:26]([CH3:27])[CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)=[C:20]2[C:15]([N:16]([CH2:32][CH:33]3[CH2:35][CH2:34]3)[C:17](=[O:31])[N:18]=[C:19]2[NH:48][CH2:43][CH2:38][OH:37])=[N:14]1

참가 물질

6

반응물 3

HCID 69879p-Chlorophenyl dichlorophosphateHCID 179901795-{2-[(6-chloroquinolin-4-yl)methyl]-7-cyclopropylmethyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carbonitrileHCID 178526901HCID 178526901, 화합물

생성물 1

HCID 10029911HCID 10029911, 화합물

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

To a solution of 5-{2-[(6-chloroquinolin-4-yl)methyl]-7-cyclopropylmethyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methyl-1H-pyrrole-3-carbonitrile (0.42 g) in pyridine (5 mL) were added 4-chlorophenyl phosphorodichloridate (0.5 mL) and 3-nitro-1,2,4 triazole (0.15 g). After heating (Tb=50° C.) for 3 h, the reaction was diluted with ethyl acetate. The organic solution was washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The residue was dissolved in THF (10 mL) and ethanolamine (1.0 mL). After 3 h, the reaction was concentrated. This residue was purified by flash chromatography using a FlashMaster™ yielding 0.22 g, ES (M+H)+=529.

후처리

  1. washThe organic solution was washed with saturated NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in THF (10 mL)
  6. concentrationthe reaction was concentrated
  7. customThis residue was purified by flash chromatography
  8. customyielding 0.22 g, ES (M+H)+=529

출처 및 근거

ORD 기록
ord-5f76ae48d7124edb887d20fd58612c2b
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371757B2

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