3-(Tributylstannanyl)pyridazine → 6-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-2-Pyridazin-3-Yl-5,6,7,8-Tetrahydro-1,6-Naphthyridine

HRID 1713124노트

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HRID 1713124 반응식
Cl[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][N:7]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH:21]4[CH2:24][CH2:23][CH2:22]4)[CH2:17][CH2:16]3)=[O:14])[CH2:6][CH2:5][C:4]=2[N:3]=1.C([Sn](CCCC)(CCCC)[C:30]1[N:31]=[N:32][CH:33]=[CH:34][CH:35]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:21]1([N:18]2[CH2:19][CH2:20][N:15]([C:13](=[O:14])[CH2:12][N:7]3[CH2:6][CH2:5][C:4]4[N:3]=[C:2]([C:30]5[N:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[CH:11]=[CH:10][C:9]=4[CH2:8]3)[CH2:16][CH2:17]2)[CH2:24][CH2:23][CH2:22]1

참가 물질

5

반응물 2

HCID 27632603-(Tributylstannanyl)pyridazineHCID 574205742-Chloro-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridine

생성물 1

HCID 574205756-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-2-Pyridazin-3-Yl-5,6,7,8-Tetrahydro-1,6-Naphthyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
110 °C

실험 절차

A mixture of 2-chloro-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridine (349 mg, 1 mmol), 3-(tributylstannyl)pyridazine (461 mg, 1.25 mmol) and Pd(PPh3)4 (116 mg, 0.1 mmol) in toluene (15 mL) is degassed by argon and heated at 110° C. in a sealed tube overnight. The mixture is cooled and saturated KF solution (10 mL) is added. The mixture is stirred at rt for 30 min, and then the layers are separated. The aqueous layer is extracted with EtOAc (15 ml) and the combined extracts are dried and evaporated. The residue is purified by PTLC to give the title compound as a white solid. MS (M+1): 393.2; 1H NMR (δ, CDCl3): 9.77 (m, 1H), 9.26 (dd, 1H), 8.05 (dd, 1H), 7.64 (d, 1H), 7.48 (d, 1H), 3.79 (s, 2H), 3.65 (q, 4H), 3.43 (s, 2H), 3.13 (t, 2H), 2.96 (t, 2H), 2.64-2.74 (m, 1H), 2.30 (q, 4H), 1.64-2.06 (m, 6H).

후처리

  1. customis degassed by argon
  2. temperatureThe mixture is cooled
  3. additionsaturated KF solution (10 mL) is added
  4. customthe layers are separated
  5. extractionThe aqueous layer is extracted with EtOAc (15 ml)
  6. customthe combined extracts are dried
  7. customevaporated
  8. customThe residue is purified by PTLC

출처 및 근거

ORD 기록
ord-496a62aa26624656bd911e22df75877a
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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