Triethylamine → HCID 59000960, compound

HRID 507309Notes

Reaction equation

HRID 507309 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20]([NH2:22])=[O:21])[CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.Cl.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20]([NH2:22])=[O:21])[CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([C:35]([C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)=[O:42])[CH2:17][CH2:18]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 59001103(2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(piperidin-4-ylmethyl)amino]-4-methyl-pentanoic acid amide

Product 1

HCID 59000960HCID 59000960, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-2-[N-(4-chlorobenzenesulfonyl)-N-(piperidin-4-ylmethyl)amino]-4-methyl-pentanoic acid amide (Example 126, 0.10 g, 0.22 mmol) and Et3N (0.06 mL, 0-5 mmol) in CH2Cl2 (3.0 mL) was added isonicotinoyl chloride hydrochloride (56 mg, 0.32 mmol). The reaction was stirred at rt for 18 h and then was poured into a mixture of EtOAc and sat. aq. NaHCO3. The organic solution was separated and washed with brine, dried over MgSO4, and concentrated to an oily residue. The residue was purified on a Biotage 10M (eluted with 80% EtOAc/hexanes) to give a white solid (36 mg, 30%). MS (ESI), (M+H)+ 509.20; 1H NMR (CDCl3, 500 MHz) δ 8.66 (br s, 2H), 7.80 (d, 1H, J=8.6), 7.73 (d, 2H, J=8.5), 7.51 (d, 2H, J=7.6), 7.41 (br s, 1H), 6.64 (br s, 1H), 5.35 (br s, 1H), 4-70 (br s, 1H), 4.10 (br s, 1H), 3.71 (br s, 1H), 3.33 (br s, 1H), 3.02 (dd, 2H, J=4.8, 16), 2.70-2.85 (br s, 1H), 1.50-2.09 (m, 5H), 1.18-1.33 (m, 4H), 0.73 (d, 3H, J=6.7), 0.68 (d, 3H, J=6.5).

Workup

  1. customThe organic solution was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oily residue
  5. customThe residue was purified on a Biotage 10M (eluted with 80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6c1c7ecbccb644358bc6453d88fd55e0
Source dataset
uspto-grants-2010_08
Patent number
US07786122B2

Reaction notes

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