Trifluoroacetic acid → 7-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-1,3,4,10a-tetrahydro-2H,9H-2,4a,5,9-tetraaza-phenanthren-10-one

HRID 1644979

反応式

HRID 1644979 の反応式
C(OC([N:8]1[CH2:21][CH2:20][N:19]2[CH:10]([C:11](=[O:36])[NH:12][C:13]3[C:18]2=[N:17][CH:16]=[C:15]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[CH2:25][CH2:24]2)[CH:14]=3)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([N:26]2[CH2:25][CH2:24][N:23]([CH2:22][C:15]3[CH:14]=[C:13]4[C:18]([N:19]5[CH:10]([C:11](=[O:36])[NH:12]4)[CH2:9][NH:8][CH2:21][CH2:20]5)=[N:17][CH:16]=3)[CH2:28][CH2:27]2)=[CH:30][CH:31]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 583243557-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-10-oxo-1,3,4,9,10,10a-hexahydro-2,4-a,5,9-tetraaza-phenanthrene-2-carboxylic acid tert-butyl ester

生成物 1

HCID 583244517-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-1,3,4,10a-tetrahydro-2H,9H-2,4a,5,9-tetraaza-phenanthren-10-one収率 8.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

7-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-10-oxo-1,3,4,9,10,10a-hexahydro-2,4a,5,9-tetraaza-phenanthrene-2-carboxylic acid tert-butyl ester (250 mg, 0.487 mmol) was dissolved in dichloromethane (5 mL) and trifluroacetic acid (3 mL) was added while stirring at room temperature. The reaction was stirred for 16 h and concentrated to a residue. The residue was dissolved in DMF and purified via HPLC (55-90% acetonitrile in water, ammonium bicarbonate buffer). The fractions were combined and concentrated until a white solid precipitated. The precipitate was filtered off and dried in vacuum to afford the title compound (17.8 mg, 8.8%) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 10.68 (s, 1H), 7.70 (d, J=2.0 Hz, 1H), 7.14-7.30 (m, 2H), 7.03 (d, J=2.0 Hz, 1H), 6.92 (d, J=9.1 Hz, 2H), 4.33 (d, J=11.4 Hz, 1H), 3.97 (dd, J=11.0, 3.4 Hz, 1H), 3.45 (dd, J=12.5, 2.9 Hz, 4H), 3.32-3.36 (m, 4H), 3.16 (d, J=9.6 Hz, 1H), 3.06-3.13 (m, 4H), 2.72-2.87 (m, 3H). [M+H] calc'd for C26H33ClN6O3, 413. found, 413.

後処理

  1. stirringThe reaction was stirred for 16 h
  2. concentrationconcentrated to a residue
  3. dissolutionThe residue was dissolved in DMF
  4. custompurified via HPLC (55-90% acetonitrile in water, ammonium bicarbonate buffer)
  5. concentrationconcentrated until a white solid
  6. customprecipitated
  7. filtrationThe precipitate was filtered off
  8. customdried in vacuum

出典と根拠

ORDレコード
ord-5fd62308e30c46c2ab7c1b9e8ce6b636
出典データセット
uspto-grants-2012_02
特許番号
US08124606B2

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