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Diisopropylethylamine → HCID 24968342、化合物

HRID 1666338
ノート
印刷プレビュー

反応式

HRID 1666338 の反応式
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[CH:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[CH2:4][CH2:3]1.[CH3:26][O:27][C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35](=O)[O:36]C2C=CC=CC=2)=[N:32][CH:33]=1.NC1C=NC(OC)=CN=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[CH3:26][O:27][C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35]([N:2]2[CH2:7][CH2:6][C:5](=[CH:8][C:9]3[CH:25]=[CH:24][CH:23]=[C:11]([O:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][N:14]=4)[CH:10]=3)[CH2:4][CH2:3]2)=[O:36])=[N:32][CH:33]=1
参加物反応条件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 81531DiisopropylethylamineHCID 145364295-Methoxypyrazin-2-amineHCID 66876115HCID 66876115、化合物HCID 668761612-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochloride

生成物 1

HCID 24968342HCID 24968342、化合物収率 75%

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

反応条件

温度
60 °C

実験手順

A solution of 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (0.371 g, 1.00 mmol) (from Example 1, Step 5) and phenyl 5-methoxypyrazin-2-ylcarbamate (0.254 g, 1.2 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 2-amino-5-methoxypyrazine) in DMSO (2.5 mL) was treated with diisopropylethylamine (0.155 g, 1.2 mmol) and was heated to 60° C. After 4 h, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with brine and dried over sodium sulfate, filtered and concentrated to a white solid. Trituration with diethyl ether provided the title compound as a white solid (365 mg, 75%). MS (APCI 10V) AP+ 486.25; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.32 (t, J=5.46 Hz, 2H) 2.44 (t, J=5.46 Hz, 2H) 3.47 (t, J=5.46 Hz, 2H) 3.54 (t, J=5.46 Hz, 2H) 3.83 (s, 3H) 6.37 (s, 1H) 7.02-7.05 (m, 2H) 7.11 (d, J=7.8 Hz, 1H) 7.21 (d, J=8.57 Hz, 1H) 7.39 (dt, J=7.6 Hz, 2 Hz, 1H) 7.99 (d, J=1.6 Hz, 1H) 8.21 (dd, J=9.2 Hz, 2.7 Hz, 1H) 8.53 (m, 2H) 9.18 (s, 1H).

後処理

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted again with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a white solid

出典と根拠

ORDレコード
ord-2e6c54e2c5ad486587076df1ada36f2c
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08044052B2

反応ノート

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