Triethylamine → HCID 57343390, compound

HRID 2276892Notes

Reaction equation

HRID 2276892 reaction equation
N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:39]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=3[Cl:47])[N:38]=[C:37]([C:48]([OH:50])=O)[C:36]=2[CH3:51])=[CH:31][CH:30]=1.[NH2:52][CH:53]1[CH2:58][CH2:57][N:56]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:55][CH2:54]1.C(N(CC)CC)C>O1CCCC1>[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[N:39]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=3[Cl:47])[N:38]=[C:37]([C:48]([NH:52][CH:53]3[CH2:54][CH2:55][N:56]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:57][CH2:58]3)=[O:50])[C:36]=2[CH3:51])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12682914-Amino-1-Boc-piperidineHCID 15194215-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 57343390HCID 57343390, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzotriazole-1-yl-oxytris(dimethylamino)phosphonium-hexafluorophosphate (BOP) (1 eq, 490 mg, 1.11 mmol) was added to a solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (1 eq, 422 mg, 1.11 mmol), tert-butyl 4-amino-1-piperidinecarboxylate (1 eq, 222 mg, 1.11 mmol), and triethylamine (3 eq., 0.46 mL, 3.32 mmol) in tetrahydrofuran (5 mL). The reaction mixture was stirred for 16 h. The reaction was concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-100% ethyl acetate/hexane to yield pure tert-butyl 4-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-amido]piperidine-1-carboxylate (548 mg, 88%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.33-1.51 (m, 9H) 1.93-2.10 (m, 2H) 2.37 (s, 3H) 2.91 (t, J=11.82 Hz, 2H) 3.89-4.23 (m, 2H) 6.84 (d, J=8.19 Hz, 1H) 7.00-7.12 (m, 2H) 7.19-7.36 (m, 4H) 7.43 (d, J=1.32 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude reaction material
  3. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c39dd2d30ad34e3bb7a5be0c074e36d8
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

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