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Dimethylformamide → HCID 68283666, 화합물

HRID 1527313
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HRID 1527313 반응식
I[C:2]1[C:10]2[C:5](=[N:6][N:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]([O:14]C)=[O:13])[N:3]=1.C(Cl)Cl.C[N:20]([CH:22]=[O:23])C>O.[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:22]([C:2]1[C:10]2[C:5](=[N:6][N:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]([OH:14])=[O:13])[N:3]=1)(=[O:23])[NH2:20]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 68283346HCID 68283346, 화합물

생성물 1

HCID 68283666HCID 68283666, 화합물

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매
HCID 962Water용매

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온도
100 °C

실험 절차

To a solution of methyl 2-(3-iodo-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetate (675 mg, 2.12 mmol) in DMF (7.5 mL) and water (1.5 mL) was added Zn(CN)2 (274 mg, 2.33 mmol), Pd2 dba3 (194 mg, 0.21 mmol) and PdCl2(dppf).CH2Cl2 adduct (173 mg, 0.21 mmol). The reaction mixture was stirred at 100° C. for 16 h. The resulting suspension was filtered and the filtrate was evaporated under vacuum. The residue was suspended in CH3CN/MeOH 1:1, the solid was filtered off and the filtrate was purified by preparative HPLC (Macherey Nagel, VP250/40, C18 Nucleosil 100-10, flow: 40 mL/min, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA) to give the title compound after lyophilisation. MS (LC/MS): 222.1 [M+H]+; tR (HPLC conditions c): 1.34 min.

후처리

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate was evaporated under vacuum
  3. filtrationthe solid was filtered off
  4. customthe filtrate was purified by preparative HPLC (Macherey Nagel, VP250/40, C18 Nucleosil 100-10, flow: 40 mL/min, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA)

출처 및 근거

ORD 기록
ord-cf1f7ed7f1454ae6aa95e116dd12de49
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085555B2

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