Potassium Carbonate → (2-{6-[8-(4-Methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-ylamino}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

HRID 1186508ノート

反応式

HRID 1186508 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.[C:24]([O:28][C:29](=[O:40])[NH:30][CH2:31][CH:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:27])([CH3:26])[CH3:25].CN(C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C.C([O-])([O-])=O.[K+].[K+]>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]>[C:24]([O:28][C:29](=[O:40])[NH:30][CH2:31][CH:32]([NH:39][C:2]1[CH:3]=[CH:4][CH:5]=[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)[N:7]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([CH3:27])([CH3:25])[CH3:26]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 2771847tert-butyl N-(2-amino-2-phenylethyl)carbamateHCID 86670919HCID 86670919、化合物

生成物 1

HCID 68226762(2-{6-[8-(4-Methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-ylamino}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

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
130 °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) (0.56 g, 1.5 mmol), (2-amino-2-phenyl-ethyl)-carbamic acid tert-butyl ester (from Example 51 supra) (0.425 g, 1.8 mmol), Pd2(dba)3 (90 mg), Davephos (120 mg), K2CO3 (0.25 g, 1.8 mmol) in dioxane (40 mL) in a sealed tube was bubbled with N2 for several minutes and then heated under N2 at 130° C. overnight. The mixture was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was first purified by chromatography (CH2Cl2:CH3OH, 100:1), then by preparative-HPLC to give (2-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-ylamino}-2-phenyl-ethyl)-carbamic acid tert-butyl ester. (Yield 30 mg, 3.8%). LC-MS: [M+H]+ 529.

後処理

  1. customwas bubbled with N2 for several minutes
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was first purified by chromatography (CH2Cl2:CH3OH, 100:1)

出典と根拠

ORDレコード
ord-b11c82af1cde4f29ad9020c15dafeda3
出典データセット
uspto-grants-2014_03
特許番号
US08673905B2

反応ノート

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