4-Chlorobenzylamine → (4-Chloro-benzyl)-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-yl}-amine

HRID 1186531ノート

反応式

HRID 1186531 の反応式
Br[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][N:15]=[C:16]([N:17]4[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]4)[C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.CN(C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C.CC([O-])(C)C.[Na+]>O1CCOCC1.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]>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([C:8]3[N:12]4[CH:13]=[CH:14][N:15]=[C:16]([N:17]5[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]5)[C:11]4=[N:10][CH:9]=3)[N:7]=2)=[CH:27][CH:26]=1

参加物

7

反応物 4

HCID 660364-ChlorobenzylamineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 86670919HCID 86670919、化合物

生成物 1

HCID 66546146(4-Chloro-benzyl)-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-yl}-amine

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-(6-bromo-pyridin-2-yl)-8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazine (from Example 39 supra) (0.373 g, 1.0 mmol), 4-chloro-benzylamine (0.14 g, 1.0 mmol), Pd2(dba)3 (60 mg), Davephos (80 mg), NaOtBu (140 mg, 1.46 mmol) suspended in dioxane (25 mL). The solution was bubbled with N2 for several minutes and then heated under N2 at 100° C. for 15 hours. The solution was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The obtained crude product was purified by preparative-HPLC to give (4-chloro-benzyl)-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-yl}-amine; hydrochloride. (Yield 31 mg, 7.1%).

後処理

  1. customThe solution was bubbled with N2 for several minutes
  2. temperatureThe solution was then cooled to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe obtained crude product
  6. customwas purified by preparative-HPLC

出典と根拠

ORDレコード
ord-7f8820c1627c4c97aa28cc5208ea8fec
出典データセット
uspto-grants-2014_03
特許番号
US08673905B2

反応ノート

読み込み中…