Morpholine → 8-Chloro-1-(5-{5-[(3,4-dichlorophenyl)methyl]-2H-tetrazol-2-yl}pentyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1097729

반응식

HRID 1097729 반응식
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]=2[N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH2:29][C:30]2[N:31]=[N:32][N:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]O)[N:34]=2)[CH:25]=[CH:26][C:27]=1[Cl:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[N:7]([CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][N:33]3[N:32]=[N:31][C:30]([CH2:29][C:24]4[CH:25]=[CH:26][C:27]([Cl:28])=[C:22]([Cl:21])[CH:23]=4)=[N:34]3)[C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]=2[N:3]=1

참가 물질

8

반응물 5

HCID 8083MorpholineHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 592995577-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dioneHCID 668129595-{5-[(3,4-dichlorophenyl)methyl]-2H-tetrazol-2-yl}-1-pentanol

생성물 1

HCID 593956058-Chloro-1-(5-{5-[(3,4-dichlorophenyl)methyl]-2H-tetrazol-2-yl}pentyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 8-chloro-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.18 g, 0.61 mmol) in THF (5 ml) was added 5-{5-[(3,4-dichlorophenyl)methyl]-2H-tetrazol-2-yl}-1-pentanol (0.191 g, 0.61 mmol; prepared in similar fashion to Example 35), triphenylphosphine (0.36 g, 1.3 mmol) and finally dibenzylazodicarboxylate (0.40 g, 1.3 mmol). The solution was stirred for 18 h after which Pd(PPh3)4 (0.16 g, 0.137 mmol) followed by morpholine (0.75 ml, 8.3 mmol) was added and the solution stirred at ambient temperature for 6 h. The solution was loaded onto an aminopropyl SPE (5 g) and eluted with MeOH then 5% AcOH/MeOH to yield the title compound containing minor impurities. Further chromatography (silica SPE, 20 g) eluting with ether yielded the title compound as a white solid (0.061 g, 18%).

후처리

  1. additionwas added
  2. washeluted with MeOH

출처 및 근거

ORD 기록
ord-4a068786fca049eea1de852f28f58bca
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143264B2

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