Triethylamine → HCID 58486395、化合物

HRID 1890767ノート

反応式

HRID 1890767 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([N:14]3[CH2:19][CH2:18][CH:17]([NH:20][CH3:21])[CH2:16][CH2:15]3)=[C:10]([CH3:22])[C:9]=2[CH3:23])=[CH:4][CH:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[C:37]([OH:39])=O)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C.CCN=C=NCCCN(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]([CH3:21])[C:37]([C@@H:32]4[CH2:33][CH2:34][CH2:35][CH2:36][N:31]4[C:29]([O:28][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:30])=[O:39])[CH2:16][CH2:15]3)=[C:10]([CH3:22])[C:9]=2[CH3:23])=[CH:4][CH:3]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516892Sodium BicarbonateHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 67368812HCID 67368812、化合物

生成物 1

HCID 58486395HCID 58486395、化合物収率 49.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Sequentially treat a solution of 1-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)-N-methylpiperidin-4-amine (100 mg, 0.318 mmol) in CH2Cl2 (3.2 mL) with (S)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (109 mg, 0.477 mmol), triethylamine (0.067 mL, 0.477 mmol) and EDCI (92 mg, 0.477 mmol). Stir the resulting mixture at ambient temperature for 2 d. Pour the reaction mixture into H2O containing NaHCO3. Separate the layers, and extract the aqueous layer with CH2Cl2. Combine the organic layers, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (gradient of 0 to 2% 2 M NH3/MeOH in CH2Cl2) to afford the title compound as a white solid (82 mg, 49%). ES/MS m/z 526.2 (M+1).

後処理

  1. customSeparate the layers
  2. extractionextract the aqueous layer with CH2Cl2
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash silica gel chromatography (gradient of 0 to 2% 2 M NH3/MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-90db35d0fbf4484c89563afc9e6d2c4d
出典データセット
uspto-grants-2013_08
特許番号
US08507490B2

反応ノート

読み込み中…