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

HRID 1713157노트

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HRID 1713157 반응식
Br[C:2]1[S:3][C:4]2[CH2:5][N:6]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH:20]4[CH2:23][CH2:22][CH2:21]4)[CH2:16][CH2:15]3)=[O:13])[CH2:7][CH2:8][C:9]=2[N:10]=1.C([Sn](CCCC)(CCCC)[C:29]1[N:30]=[N:31][CH:32]=[CH:33][CH:34]=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:20]1([N:17]2[CH2:18][CH2:19][N:14]([C:12](=[O:13])[CH2:11][N:6]3[CH2:7][CH2:8][C:9]4[N:10]=[C:2]([C:29]5[N:30]=[N:31][CH:32]=[CH:33][CH:34]=5)[S:3][C:4]=4[CH2:5]3)[CH2:15][CH2:16]2)[CH2:23][CH2:22][CH2:21]1

참가 물질

5

반응물 2

HCID 27632603-(Tributylstannanyl)pyridazineHCID 574205862-Bromo-5-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine

생성물 1

HCID 574207635-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-2-Pyridazin-3-Yl-4,5,6,7-Tetrahydro[1,3]Thiazolo[5,4-C]Pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
110 °C

실험 절차

A mixture of 2-bromo-5-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine (300 mg, 0.75 mmol), 3-(tributylstannyl)pyridazine (369 mg, 1 mmol) and Pd(PPh3)4 (92 mg, 0.08 mmol) in toluene (15 mL) is degassed by Ar 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 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 white solid. MS (M+1): 399.2; 1H NMR (δ, CDCl3): 9.63-9.64 (m, 1H), 9.23 (dd, 1H), 7.84 (dd, 1H), 3.90 (s, 2H), 3.62 (td, 4H), 3.45 (s, 2H), 3.00 (s, 4H), 2.64-2.74 (m, 1H), 2.29 (t, 4H), 1.64-2.06 (m, 6H).

후처리

  1. customis degassed by Ar
  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-3ab5a6f2906844f1acd0b80e8b705bf8
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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