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O-Phenylenediamine → HCID 59605532, 화합물

HRID 1922804
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HRID 1922804 반응식
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][N:13]3[CH2:16][CH:15]([CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:14]3)[N:8]2[CH3:11])=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:3]=1.[C:29]1([NH2:36])[C:30]([NH2:35])=[CH:31][CH:32]=[CH:33][CH:34]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.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]>[CH3:11][N:8]1[C:7]([CH2:12][N:13]2[CH2:16][CH:15]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:14]2)=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH:35][C:30]1[C:29]([NH2:36])=[CH:34][CH:33]=[CH:32][CH:31]=1)=[N:3][C:4]=2[N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7243O-PhenylenediamineHCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 59605752HCID 59605752, 화합물

생성물 1

HCID 59605532HCID 59605532, 화합물수율 80.2%

시약·촉매·용매 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-chloro-9-methyl-6-morpholin-4-yl-8-[3-(tetrahydropyran-4-yl)azetidin-1-ylmethyl]-9H-purine (0.25 g, 0.61 mmol), benzene-1,2-diamine (0.133 g, 1.23 mmol), Xphos (0.059g, 0.123 mmol), Pd2(dba)3 (0.028 g, 0.031 mmol) and Cs2CO3 (0.17 g, 1.23 mmol) in DMF (2.5 mL) was subjected to microwave irradiation at 150° C. for 30 min. The suspension was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, MEOH:DCM, gradient 0:100 to 10:90) to give the title compound as a brown foam (0.234 g, 80%)._LCMS (Method A): RT=2.20 min, [M+H]+ 479.4

후처리

  1. customirradiation at 150° C. for 30 min
  2. filtrationThe suspension was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (Si—PPC, MEOH:DCM, gradient 0:100 to 10:90)

출처 및 근거

ORD 기록
ord-bac1ca116014444ca7e66a7a733dddc4
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173650B2

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