Triethylamine → Cyclohexanecarboxylic acid [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-amide

HRID 1827537Notes

Reaction equation

HRID 1827537 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:32]=[C:31]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:30]=[CH:29][C:12]=1[CH2:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:10][C:11]1[CH:32]=[C:31]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:30]=[CH:29][C:12]=1[CH2:13][N:14]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)=[CH:17][CH:16]=1)[C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 22137435(2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Product 1

HCID 86760097Cyclohexanecarboxylic acid [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-amideYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cyclohexanecarbonyl chloride (990 mg, 6.75 mmol) in methylene chloride (30 mL) was added a mixture of (2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (1.94 g, 4.5 mmol) and triethylamine (1.3 mL, 9.0 mmol) in methylene chloride (15 mL) dropwise. The reaction mixture was stirred at room temperature for 24 hr. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution and the aqueous solution was washed with methylene chloride. The organic solution was dried (sodium sulfate), filtered and concentrated in vacuo. The crude product was purified by Biotage® chromatography using 5% methanol/methylene chloride to afford the title compound of Step A as an oil (2.12 g). MS 541.3 (M+1)+

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate solution
  2. washthe aqueous solution was washed with methylene chloride
  3. dry with materialThe organic solution was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by Biotage® chromatography

Sources & evidence

ORD record
ord-7d3978a5de3d46ecb8664dbe8c84a661
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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