Triethylamine → 1-[2-(2-Chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidin-7-yl]-4-ethylaminopiperidine-4-carboxylic Acid Amide

HRID 348026Notes

Reaction equation

HRID 348026 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:10]([I:11])=[C:6]2[N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:26]([NH:28][C:29]1([C:35]([NH2:37])=[O:36])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:27]>C(O)C.C(Cl)Cl>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[C:10]([I:11])=[C:6]2[N:5]=[CH:4][CH:3]=[C:2]([N:32]3[CH2:31][CH2:30][C:29]([NH:28][CH2:26][CH3:27])([C:35]([NH2:37])=[O:36])[CH2:34][CH2:33]3)[N:7]2[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 965734-(Ethylamino)piperidine-4-carboxamideHCID 21083717HCID 21083717, compound

Product 1

HCID 588013111-[2-(2-Chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidin-7-yl]-4-ethylaminopiperidine-4-carboxylic Acid AmideYield 86.2%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of 7-chloro-2-(2-chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidine (I-1A-1d; 80 mg, 0.21 mmol) and triethylamine (44 μl, 0.32 mmol) in 1:1 ethanol/methylene chloride (2 ml) was added 4-ethylaminopiperidine-4-carboxylic acid amide (I-1A-1g; 40 mg, 0.23 mmol). A colorless precipitate formed after several minutes and the mixture was stirred overnight. The solid precipitate was isolated by vacuum filtration, washed with ethanol and ether, and then dried, in vacuo, to afford product I-1A-1h as an off-white solid (95 mg, 86%): +APcI MS (M+1) 525.4; 1H NMR (400 MHz, CD3OD) δ 8.27 (d, J=5.4 Hz, 1H), 7.55 (d, J=7.5 Hz, 1H), 7.48–7.39 (m, 3H), 6.45 (d, J=5.6 Hz, 1H), 4.14–3.96 (m, 2H), 3.92–3.84 (m, 2H), 2.50 (q, J=7.1 Hz, 2H), 2.23–2.15 (m, 2H), 1.85–1.77 (m, 2H), 1.16 (t, J=7.1 Hz, 3H).

Workup

  1. customA colorless precipitate formed after several minutes
  2. customThe solid precipitate was isolated by vacuum filtration
  3. washwashed with ethanol and ether
  4. customdried, in vacuo

Sources & evidence

ORD record
ord-e39ffc333d784b1fb85888f75b243bf4
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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