Triethylamine → HCID 22063871, compound

HRID 1828177Notes

Reaction equation

HRID 1828177 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.Cl.[NH2:15][CH:16]([C:35]1[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=1)[CH:17]([C:19]1[CH:34]=[CH:33][C:22]2[N:23]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:24](=[O:27])[N:25]([CH3:26])[C:21]=2[CH:20]=1)[OH:18].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.O>[CH:28]1([N:23]2[C:22]3[CH:33]=[CH:34][C:19]([CH:17]([OH:18])[CH:16]([NH:15][C:5](=[O:7])[CH2:4][CH2:3][O:2][CH3:1])[C:35]4[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=4)=[CH:20][C:21]=3[N:25]([CH3:26])[C:24]2=[O:27])[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1344423-Methoxypropionic acidHCID 22063875HCID 22063875, compound

Product 1

HCID 22063871HCID 22063871, compoundYield 96.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-methoxypropionic acid (93.5 μL, 0.99 mmol) in methylene chloride (6 mL) and DMF (200 μL) was added oxalyl chloride (86.8 μL, 0.99 mmol). The resulting clear solution was stirred for 2 hours, then added via canula to a stirred solution of 5-(2-amino-1-hydroxy-2-m-tolyl-ethyl)-1-cyclopentyl-3-methyl-1,3-dihydro-benzoimidazol-2-one hydrochloride (400 mg, 0.99 mmol) and triethyl amine (306 μL) in methylene chloride (4 mL). After 1 hour, LCMS showed complete reaction. Water was added to the reaction mixture and the organic phase was separated and washed with brine. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo to afford 433 mg of the amide, which was used without further purification.

Workup

  1. waitAfter 1 hour
  2. customreaction
  3. customthe organic phase was separated
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d589c7cbe364ccbb07160c8cc527fb6
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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