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Acetic Acid → 4-(8-(4-((Dimethylamino)methyl)phenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-9-yl)-N,N-dimethylbenzamide

HRID 1467680
ノート
印刷プレビュー

反応式

HRID 1467680 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[NH:21][C:19]3[C:20]4[C:11](=[N:12][NH:13][C:14](=[O:22])[C:15]=4[CH:16]=[CH:17][CH:18]=3)[CH:10]2[C:23]2[CH:33]=[CH:32][C:26]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])=[CH:25][CH:24]=2)=[CH:5][CH:4]=1)=O.C(O)(=O)C.[CH3:38][NH:39][CH3:40].[BH4-].[Na+]>C(Cl)Cl>[CH3:38][N:39]([CH2:1][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[NH:21][C:19]3[C:20]4[C:11](=[N:12][NH:13][C:14](=[O:22])[C:15]=4[CH:16]=[CH:17][CH:18]=3)[CH:10]2[C:23]2[CH:24]=[CH:25][C:26]([C:27]([N:29]([CH3:30])[CH3:31])=[O:28])=[CH:32][CH:33]=2)=[CH:7][CH:8]=1)[CH3:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 4311764Sodium borohydrideHCID 1363447484-(8-(4-Formylphenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-9-yl)-N,N-dimethylbenzamide

生成物 1

HCID 1363746814-(8-(4-((Dimethylamino)methyl)phenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-9-yl)-N,N-dimethylbenzamide収率 10%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 4-(8-(4-formylphenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-9-yl)-N,N-dimethylbenzamide (140 mg, 0.32 mmol) in dried DCM (20 mL) was added acetic acid followed by dimethylamine (57 mg, 1.3 mmol). After the addition, the mixture was stirred at room temperature overnight. Then the mixture was cooled to 0° C. Sodium borohydride (102 mg, 0.48 mmol) was added. After the addition, the mixture was stirred at this temperature for 12 hr. DCM was removed under reduced pressure. The residue was washed with ethyl acetate/methanol (10/1) and filtered. The filtrate was concentrated to give the crude product, which was purified by prep-HPLC to give the title compound as a white solid (15 mg, yield 10%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 2.19 (dd, 6H), 2.93 (s, 314), 3.06 (s, 3H), 3.40 (dd, 2H), 4.34 (d, 1H), 4.16-7.19 (m, 5H), 7.23-7.26 (m, 4H), 7.54 (d, 1H), 7.61 (t, 1H). LC-MS (ESI) m/z: 468 (M+1)+.

後処理

  1. additionAfter the addition
  2. temperatureThen the mixture was cooled to 0° C
  3. additionAfter the addition
  4. stirringthe mixture was stirred at this temperature for 12 hr
  5. customDCM was removed under reduced pressure
  6. washThe residue was washed with ethyl acetate/methanol (10/1)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customto give the crude product, which
  10. customwas purified by prep-HPLC

出典と根拠

ORDレコード
ord-9cd3d27e476c46ed919f1843e5abc5cc
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08999987B2

反応ノート

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