Hydrazine → 3-Amino-N-[4-(3-aminocyclohexyl)pyridin-3-yl]-7-ethylquinoline-2-carboxamide

HRID 924412ノート

反応式

HRID 924412 の反応式
[NH2:1][C:2]1[C:3]([C:14]([OH:16])=O)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([CH2:12][CH3:13])[CH:6]=2.[NH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH:24]1[CH2:29][CH2:28][CH2:27][CH:26]([N:30]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[OH-].[Na+].NN>CN(C=O)C.CO>[NH2:1][C:2]1[C:3]([C:14]([NH:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:23]=2[CH:24]2[CH2:29][CH2:28][CH2:27][CH:26]([NH2:30])[CH2:25]2)=[O:16])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([CH2:12][CH3:13])[CH:6]=2

参加物

9

反応物 6

HCID 9321HydrazineHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59226443HCID 59226443、化合物HCID 867268773-Amino-7-ethylquinoline-2-carboxylic acid

生成物 1

HCID 778440263-Amino-N-[4-(3-aminocyclohexyl)pyridin-3-yl]-7-ethylquinoline-2-carboxamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A mixture of 3-amino-7-ethylquinoline-2-carboxylic acid (0.040 g, 0.18 mmol), 2-[3-(3-aminopyridin-4-yl)cyclohexyl]-1H-isoindole-1,3(2H)-dione (0.055 g, 0.17 mmol), HATU (0.22 g, 0.58 mmol), DMF (0.65 mL) and DIPEA (0.076 g, 0.59 mmol) was stirred at room temperature for 16 h. Aq. NaOH (1 M) was added to the reaction mixture, and a precipitate formed, which was collected by vacuum filtration. The collected solid was washed with 1 M NaOH, followed by water and dried under vacuum to afford an intermediate. The intermediate was dissolved in DMF (0.15 mL) and hydrazine (0.15 mL) was added. The resulting reaction mixture was stirred at room temperature for 16 h, diluted with MeOH, filtered and purified by preparative LC MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min., eluting with a gradient of MeCN and water with 0.15% NH4OH) to give title compound. LCMS calc. for C23H28N5O (M+H)+: m/z=390.2. Found: 390.1.

後処理

  1. customa precipitate formed
  2. filtrationwhich was collected by vacuum filtration
  3. washThe collected solid was washed with 1 M NaOH
  4. customdried under vacuum
  5. customto afford an intermediate
  6. customThe resulting reaction mixture
  7. stirringwas stirred at room temperature for 16 h
  8. filtrationfiltered
  9. custompurified by preparative LC MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min.
  10. washeluting with a gradient of MeCN and water with 0.15% NH4OH)

出典と根拠

ORDレコード
ord-d6bef013f78a4cb2a31fb30abe8712eb
出典データセット
uspto-grants-2016_03
特許番号
US09278950B2

反応ノート

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