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 1186508노트

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HRID 1186508 반응식
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]

참가 물질

7

반응물 4

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

생성물 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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
130 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b11c82af1cde4f29ad9020c15dafeda3
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673905B2

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