Triethylamine → HCID 71571028, compound

HRID 714548Notes

Reaction equation

HRID 714548 reaction equation
OC(C(F)(F)F)=O.[NH:8]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]2[CH2:20][CH2:19][CH:18]([C:21]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[O:22])[CH2:17][CH2:16]2)[CH2:10][CH2:9]1.CCN(CC)CC.Cl[C:36]([O:38][CH2:39][C:40]#[CH:41])=[O:37]>C(Cl)Cl>[CH2:39]([O:38][C:36]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]2[CH2:20][CH2:19][CH:18]([C:21](=[O:22])[NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=[O:37])[C:40]#[CH:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3356829Propargyl chloroformateHCID 131734059HCID 131734059, compound

Product 1

HCID 71571028HCID 71571028, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(azepan-4-yl)-N-(2-methylpropyl)piperidine-4-carboxamide TFA salt (0.15 g, 0.38 mmol) was dissolved in DCM (8 mL) at rt. NEt3 (0.16 mL, 1.14 mmol) and propargyl chloroformate (0.06 mL, 0.57 mmol) were added and the reaction mixture was stirred at rt for 2 h under nitrogen. The solvents were removed in vacuo, and the residue was partitioned between DCM and sat. NaHCO3 sol.), organic layer washed with sat. NaCl sol. and dried over MgSO4. The residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 10 g, 40-63 μm, 60 Å, 12 mL per min, gradient 0% to 10% MeOH in DCM]) to give prop-2-yn-1-yl-4-(4-((2-methylpropyl)carbamoyl)piperidin-1-yl)azepane-1-carboxylate (0.04 g, 31%) as a yellow gum.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was partitioned between DCM and sat. NaHCO3 sol.), organic layer
  3. washwashed with sat. NaCl sol.
  4. dry with materialdried over MgSO4
  5. customThe residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 10 g, 40-63 μm, 60 Å, 12 mL per min, gradient 0% to 10% MeOH in DCM])

Sources & evidence

ORD record
ord-fa98844cdb7c47e090c45c0088fe1a1f
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

Loading…