Triethylamine → HCID 57342714, compound

HRID 2276882Notes

Reaction equation

HRID 2276882 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]([OH:23])=O)[C:9]=2[CH3:24])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:32]([NH:34][C:35]1([C:41]([NH2:43])=[O:42])[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[CH3:33].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][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]([N:38]3[CH2:37][CH2:36][C:35]([NH:34][CH2:32][CH3:33])([C:41]([NH2:43])=[O:42])[CH2:40][CH2:39]3)=[O:23])[C:9]=2[CH3:24])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 965734-(Ethylamino)piperidine-4-carboxamideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 15194215-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 57342714HCID 57342714, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carb oxylic acid (1 eq, 20 mg, 0.052 mmol), triethylamine (3 eq, 0.02 mL, 0.157 mmol), 4-(ethylamino)-4-piperidinecarboxamide (1 eq, 9 mg, 0.052 mmol), and benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (1 eq, 23 mg, 0.052 mmol) was stirred in tetrahydrofuran (5 mL) for 16 h. The reaction was concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-100% CMA 80/ethyl acetate and precipitated from ethyl acetate with hexane to yield pure 1-{[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-(ethylamino)piperidine-4-carboxamide (13 mg, 46%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.10 (t, J=6.97 Hz, 3H) 1.61-1.80 (m, 2H) 2.08-2.26 (m, 5H) 2.45-2.63 (m, 2H) 3.68 (td, J=8.85, 4.43 Hz, 2H) 3.96-4.19 (m, 2H) 5.40 (br. s., 1H) 7.07 (d, J=8.29 Hz, 2H) 7.12-7.19 (m, 1H) 7.20-7.36 (m, 3H) 7.44 (d, J=1.98 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude reaction material
  3. customwas then purified by silica gel column chromatography
  4. customprecipitated from ethyl acetate with hexane

Sources & evidence

ORD record
ord-cea447a88f1345df9f5fe398319a2347
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

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