Binap, (A+-)- → 4-Chloro-6-(3-piperidin-1-ylmethyl-benzylamino)-2H-phthalazin-1-one

HRID 1667428

反応式

HRID 1667428 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].[N:14]1([CH2:20][C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[CH2:24][NH2:25])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>CC(N(C)C)=O.CCOC(C)=O.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]>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:25][CH2:24][C:23]3[CH:26]=[CH:27][CH:28]=[C:21]([CH2:20][N:14]4[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]4)[CH:22]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

参加物

8

反応物 4

HCID 634876Binap, (A+-)-HCID 27946783-Piperidin-1-ylmethyl-benzylamineHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

生成物 1

HCID 584473524-Chloro-6-(3-piperidin-1-ylmethyl-benzylamino)-2H-phthalazin-1-one

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (70 mg, 0.27 mmol), 3-piperidin-1-ylmethyl-benzylamine (72 mg, 0.35 mmol), Pd2(dba)3 (25 mg, 0.027 mmol), rac-BINAP (51 mg, 0.081 mmol) and NaOt-Bu (76 mg, 0.81 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-(3-piperidin-1-ylmethyl-benzylamino)-2H-phthalazin-1-one: 16 mg (15.5%): m/z (M+H)=383. 1H-NMR (DMSO-d6) δ: 12.30 (s, 1H), 7.95 (d, 1H), 7.63 (m, 1H), 7.25 (m, 3H), 7.15 (m, 2H), 6.75 (s, 1H), 4.41 (d, 2H), 3.37 (s, 2H), 2.24 (m, 4H), 1.38 (m, 4H), 1.32 (m, 2H).

後処理

  1. temperatureto cool
  2. washwashed with water (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-abf262d810e54e39bd412ecdac26a62c
出典データセット
uspto-grants-2011_10
特許番号
US08044041B2

関連ノート

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