Triethylamine → HCID 71116126, compound

HRID 2276900Notes

Reaction equation

HRID 2276900 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]([N:23]3[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]3)=[O:22])[C:9]=2[CH3:30])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[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]([N:23]3[CH2:24][CH2:25][CH:26]([NH:29][S:39]([CH3:38])(=[O:41])=[O:40])[CH2:27][CH2:28]3)=[O:22])[C:9]=2[CH3:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71116108HCID 71116108, compound

Product 1

HCID 71116126HCID 71116126, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}piperidin-4-amine (20 mg, 0.043 mmol, 1 eq.), triethylamine (0.02 mL, 0.129 mmol, 3 eq.), and the methanesulfonyl chloride (0.007 mL, 0.086 mmol, 2 eq.) were stirred in dichloromethane (2 mL) for 16 h. The reaction was concentrated in vacuo. The crude material was purified by column chromatography 0-100% ethyl acetate/hexanes to yield 17 mg (74%) of desired product. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.60 (dd, J=14.60, 7.06 Hz, 2H) 2.05-2.36 (m, 5H) 2.93-3.10 (m, 3H) 3.35-3.76 (m, 2H) 4.45 (br. s., 2H) 4.71 (br. s., 1H) 7.07 (d, J=7.91 Hz, 2H) 7.15 (d, J=7.72 Hz, 1H) 7.20-7.35 (m, 3H) 7.45 (s, 1H); [M+H]+ 541.3.

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-5daf4bfb99e6496391392fdcecc1d551
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

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