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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
Notes
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Reaction equation

HRID 348028 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d8d39118e3a049a59718fde3598015b7
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176210B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes