反応式
[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[O:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[N:20]=[C:21]([NH2:24])[S:22][CH:23]=2)[CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:24][C:21]2[S:22][CH:23]=[C:19]([CH2:18][N:15]3[CH2:16][CH2:17][O:12][CH2:13][CH2:14]3)[N:20]=2)=[N:4][CH:3]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 90 °C
実験手順
Intermediate 3 (5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine, 140 mg, 0.50 mmol), Intermediate 6 (4-(1-morpholinomethyl) thiazol-2-ylamine, 120 mg, 0.60 mmol), sodium tert-butoxide (68 mg, 0.71 mmol), palladium dibenzylidene acetone (19 mg, 0.02 mmol) and Xantphos (23 mg, 0.04 mmol) were suspended in toluene (4 mL). The mixture is degassed with nitrogen for 5 min and then stirred at 90° C. for 16 h. The solvent is evaporated in vacuo to leave a brown residue. The residue is purified by column chromatography, eluting with 2% methanolic ammonia (7 N) in dichloromethane to give the title compound as a yellow powder (53 mg, 27%). 1H NMR (400 MHz, d6-DMSO) δ 2.53 (s, 4H, CH2CH2), 3.51 (s, 2H, CH2), 3.61 (m, 4H, CH2CH2), 6.99 (s, 1H), 8.13 (s, 1H), 8.61 (s, 1H), 8.75 (s, 1H).
後処理
- customThe mixture is degassed with nitrogen for 5 min
- customThe solvent is evaporated in vacuo
- customto leave a brown residue
- customThe residue is purified by column chromatography
- washeluting with 2% methanolic ammonia (7 N) in dichloromethane
出典と根拠
- ORDレコード
- ord-f85e440e0c1a4d139be12b587a351691
- 出典データセット
- uspto-grants-2012_04
- 特許番号
- US08148369B2
関連ノート
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