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Diisopropylethylamine → 1-[3-(4-Chlorophenyl)-2-(2-chlorophenyl)-6-methylpyrazolo[1,5-a]pyrimidin-7-yl]-4-ethylaminopiperidine-4-carboxylic Acid Amide

HRID 348028
ノート
印刷プレビュー

反応式

HRID 348028 の反応式
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:6]2[N:5]=[CH:4][C:3]=1[CH3:25].C(N(C(C)C)CC)(C)C.[CH2:35]([NH:37][C:38]1([C:44]([NH2:46])=[O:45])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)[CH3:36]>C1COCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[N:8][N:7]3[C:2]([N:41]4[CH2:40][CH2:39][C:38]([NH:37][CH2:35][CH3:36])([C:44]([NH2:46])=[O:45])[CH2:43][CH2:42]4)=[C:3]([CH3:25])[CH:4]=[N:5][C:6]=23)=[CH:12][CH:13]=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

5

反応物 3

HCID 81531DiisopropylethylamineHCID 965734-(Ethylamino)piperidine-4-carboxamideHCID 210837227-Chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-6-methylpyrazolo[1,5-a]pyrimidine

生成物 1

HCID 100754641-[3-(4-Chlorophenyl)-2-(2-chlorophenyl)-6-methylpyrazolo[1,5-a]pyrimidin-7-yl]-4-ethylaminopiperidine-4-carboxylic Acid Amide

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
50 °C

実験手順

To a solution of 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-6-methylpyrazolo[1,5-a]pyrimidine (I-3A-1d; 31.3 mg, 0.0806 mmol) and diisopropylethylamine (0.025 ml, 0.14 mmol) in THF (1 ml) was added 4-ethylaminopiperidine-4-carboxylic acid amide (I-1A-1g; 18.5 mg, 0.108 mmol). The mixture was stirred at 50° C. for 20 hours. After cooling to room temperature, the reaction was extracted from saturated aqueous NaHCO3 with ethyl acetate, the combined organic layers were dried (MgSO4), concentrated and purified on a Biotage™ Flash 12S column using 0–5% methanol in methylene chloride as eluant to afford, after trituration from hexanes/methylene chloride, product 3A-1 as a solid (29 mg, 69%): +ESI MS (M+1) 523.4; 1H NMR (400 MHz, CD3OD) δ 8.24 (s, 1H), 7.48–7.34 (m, 6H), 7.21 (d, J=8.7 Hz, 2H), 3.82–3.74 (m, 2H), 3.66–3.58 (m, 2H), 2.51 (q, J=7.1 Hz, 2H), 2.39 (s, 3H), 2.28–2.20 (m, 2H), 1.88–1.80 (m, 2H), 1.10 (t, J=7.1 Hz, 3H).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction was extracted from saturated aqueous NaHCO3 with ethyl acetate
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified on a Biotage™ Flash 12S column
  6. customto afford

出典と根拠

ORDレコード
ord-d8d39118e3a049a59718fde3598015b7
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176210B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート