Hydrochloric Acid → 9-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60216노트

반응식

HRID 60216 반응식
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23](Br)[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.C(OCC)(=O)C.Cl>[Pd].C(N(CC)CC)C.CN(C=O)C>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[CH:23][CH:24]=[N:25][C:11]2=3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8857Ethyl AcetateHCID 582664728-(Benzenesulfonyl)-12-bromo-3-hydroxy-5,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2,4,6,10,12-hexaene-4-carbonitrile

생성물 1

HCID 582663029-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile수율 89%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

A mixture of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (9.91 g, 23.1 mmol), palladium on carbon hydrogenation catalyst (10 wt %, 1.0 g, 0.94 mmol), ethanol (250 mL), ethyl acetate (50 mL), DMF (50 mL) and triethylamine (50 mL) was stirred at room temperature under an atmosphere of hydrogen for 16 hours. The catalyst was removed by filtration through Celite© and the filtrate evaporated to dryness to give a gum, that was mixed with hydrochloric acid (1M, 100 mL) and sonicated in a laboratory ultrasonic cleaning bath for 30 minutes. The resultant solid was collected by filtration, washed with water then dried under vacuum to afford the title compound as a tan coloured solid (7.19 g, 89%). 1H NMR (400 MHz, DMSO-d6): 9.27 (s, 1H), 8.71 (dd, J=4.9, 1.7 Hz, 1H), 8.68 (dd, J=7.9, 1.7 Hz, 1H), 8.20-8.20 (m, 2H), 7.74-7.73 (m, 1H), 7.60-7.59 (m, 3H).

후처리

  1. customThe catalyst was removed by filtration through Celite©
  2. customthe filtrate evaporated to dryness
  3. customto give a gum, that
  4. customsonicated in a laboratory
  5. customfor 30 minutes
  6. filtrationThe resultant solid was collected by filtration
  7. washwashed with water
  8. customthen dried under vacuum

출처 및 근거

ORD 기록
ord-64fcaa30da704c2cabb77b0d31134ccd
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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