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 1713157ノート

反応式

HRID 1713157 の反応式
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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3ab5a6f2906844f1acd0b80e8b705bf8
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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