Water → HCID 178449875、化合物

HRID 82765ノート

反応式

HRID 82765 の反応式
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:23])[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2F)/[N:7]([CH2:24][C@H:25]2[CH2:29][CH2:28][CH2:27][O:26]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[C:31]([NH:35][NH2:36])([CH3:34])([CH3:33])[CH3:32].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:31]([NH:35][NH:36][C:13]1[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:19])[F:20])=[CH:17][C:12]=1[C:11](/[N:10]=[C:8]1\[S:9][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:6][N:7]\1[CH2:24][C@H:25]1[CH2:29][CH2:28][CH2:27][O:26]1)=[O:23])([CH3:34])([CH3:33])[CH3:32]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81889tert-Butylhydrazine monohydrochlorideHCID 178441320HCID 178441320、化合物

生成物 1

HCID 178449875HCID 178449875、化合物収率 20.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of Example 1A (300 mg, 0.7 mmol), tert-butylhydrazine hydrochloride (261 mg, 2.1 mmol) and potassium carbonate (385 mg, 2.8 mmol) in DMF (15 mL) was stirred at 40° C. for 24 hours. The mixture was poured into water and extracted with ethyl acetate. The acetate extract was washed with water, brine, dried with MgSO4, and concentrated under reduced pressure. Purification by chromatography (SiO2) afforded 70 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.08 (s, 9 H), 1.30-1.35 (m, 9H), 1.63-2.04 (m, 4 H), 3.68 (t, J=6.7 Hz, 1 H), 3.76-3.88 (m, 1 H), 4.18-4.39 (m, 3 H), 4.62 (s, 1 H), 7.28-7.32 (m, 1 H), 7.46-7.60 (m, 2 H), 8.51 (d, J=1.6 Hz, 1 H), 9.90 (s, 1 H). MS (DCI/NH3) m/z 499 (M+H)+. Anal. calculated for C24H33F3N4O2S: C, 57.81H, 6.67 N, 11.24. Found: C, 58.22H, 6.72 N, 10.98.

後処理

  1. extractionextracted with ethyl acetate
  2. extractionThe acetate extract
  3. washwas washed with water, brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by chromatography (SiO2)

出典と根拠

ORDレコード
ord-fbce008db9404f73b3834b899d96f58c
出典データセット
uspto-grants-2014_09
特許番号
US08846730B2

反応ノート

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