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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
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HRID 348028 반응식
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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d8d39118e3a049a59718fde3598015b7
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07176210B2

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