Triethylamine → HCID 57343721, compound

HRID 2276896Notes

Reaction equation

HRID 2276896 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[O:22])[C:9]=2[CH3:30])=[CH:4][CH:3]=1.Cl[C:32]([O:34][C:35]1C=CC([N+]([O-])=O)=C[CH:36]=1)=[O:33].C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][CH:24]3[CH2:29][CH2:28][N:27]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:26][CH2:25]3)=[O:22])[C:9]=2[CH3:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 57343391HCID 57343391, compound

Product 1

HCID 57343721HCID 57343721, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-4-yl)-1H-pyrazole-3-carboxamide (1 eq, 61 mg, 0.132 mmol), p-nitrophenyl chloroformate (1.1 eq, 29 mg, 0.144 mmol), and triethylamine (3 eq, 0.06 mL, 0.395 mmol) were stirred for 16 h in THF (2 mL). The reaction was concentrated in vacuo. The crude material was purified by column chromatography 0-100% ethyl acetate/hexanes to yield 62 mg (75%) of desired product 4-nitrophenyl 4-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-amido]piperidine-1-carboxylate. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.54-1.74 (m, 2H) 2.18 (br s, 2H) 2.42 (s, 3H) 3.04-3.38 (m, 2H) 4.21-4.43 (m, 3H) 6.95 (d, J=7.91 Hz, 1H) 7.10 (d, J=8.29 Hz, 2H) 7.30-7.41 (m, 5H) 7.47 (s, 1H) 8.29 (d, J=9.04 Hz, 2H); [M+H]+ 628.7.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude material was purified by column chromatography 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8faa94ec31414227a9a7a7758e872e72
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

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