Morpholine → (R)-(3-methyl-4-(4-morpholinophthalazin-1-yl)piperazin-1-yl)(phenyl)methanone

HRID 1689971ノート

反応式

HRID 1689971 の反応式
CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2(P(C3C=CC=CC=3)C3C=CC=CC=3)CC=C3C(C=CC=C3)=C2C2C3C(=CC=CC=3)C=CC=2)C=CC=CC=1.Cl[C:54]1[C:63]2[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=2)[C:57]([N:64]2[CH2:69][CH2:68][N:67]([C:70]([C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)=[O:71])[CH2:66][C@H:65]2[CH3:78])=[N:56][N:55]=1.[NH:79]1[CH2:84][CH2:83][O:82][CH2:81][CH2:80]1>ClCCl.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]>[CH3:78][C@H:65]1[N:64]([C:57]2[C:58]3[C:63](=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:54]([N:79]3[CH2:84][CH2:83][O:82][CH2:81][CH2:80]3)=[N:55][N:56]=2)[CH2:69][CH2:68][N:67]([C:70]([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)=[O:71])[CH2:66]1

参加物

7

反応物 4

HCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 57581487(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanoneHCID 86595863(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl

生成物 1

HCID 66904757(R)-(3-methyl-4-(4-morpholinophthalazin-1-yl)piperazin-1-yl)(phenyl)methanone

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

Compound 66 was prepared as described in general method E. Sodium t-butoxide (0.0550 g, 0.572 mmol), rac-2,2-bis(diphenylphosphino)-1,1-binaphthalene (0.0102 g, 0.0164 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.00749 g, 0.00818 mmol), and (R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone JK-5 (0.150 g, 0.409 mmol) were combined in a screw cap vial, purged to argon, and solvated with degassed morpholine (0.142 mL, 1.64 mmol). The reaction vial was sealed and stirred at 80° C. After 16 h, the reaction was taken up in dichloromethane and directly loaded onto silica gel. Purification by column chromatography (gradient elution 40 to 100% ethyl acetate in hexanes) afforded 66. MS (M+H)+=418.1.

後処理

  1. customCompound 66 was prepared
  2. customcap vial
  3. custompurged to argon
  4. customThe reaction
  5. customvial was sealed
  6. customPurification
  7. washby column chromatography (gradient elution 40 to 100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-fe40f602191d402fafc846fd49d0d13a
出典データセット
uspto-grants-2012_04
特許番号
US08153633B2

反応ノート

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