Triethylamine → HCID 68777565, compound

HRID 1711143Notes

Reaction equation

HRID 1711143 reaction equation
[C:1]([CH2:5][C:6]([OH:8])=O)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[C:15]([O:19][C:20](=[O:41])[NH:21][CH2:22][CH2:23][CH:24]([N:26]1[CH2:31][CH2:30][CH:29]([NH:32][CH2:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][C:39]=2[CH3:40])[CH2:28][CH2:27]1)[CH3:25])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.O1CCCC1>[C:15]([O:19][C:20](=[O:41])[NH:21][CH2:22][CH2:23][CH:24]([N:26]1[CH2:31][CH2:30][CH:29]([N:32]([C:6](=[O:8])[CH2:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][C:39]=2[CH3:40])[CH2:28][CH2:27]1)[CH3:25])([CH3:18])([CH3:16])[CH3:17]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14057tert-Butylacetic acidHCID 65578Oxalyl chlorideHCID 68773461HCID 68773461, compound

Product 1

HCID 68777565HCID 68777565, compoundYield 60.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butylacetic acid (63 μL, 0.50 mmol) and DMF (3 drops) in methylene chloride (4 ml) was added oxalyl chloride (115 μL, 1.32 mmol) and the resulting orange solution was stirred at 25° C. for 3 hours. The solvent was removed in vacuo to give an orange residue. (3-{4-[(4-Methyl-pyridin-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (0.125 g, 0.33 mmol) and triethylamine (115 μL, 0.83 mmol) dissolved in tetrahydrofuran (5 ml) were added to the flask containing the orange residue and the resulting mixture was stirred at 50° C. for 12 hours. Standard basic workup gave the crude product as an orange oil. Purification by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 93:5:2, v/v/v) afforded (3-{4-[(3,3-dimethyl-butyryl)-(4-methyl-pyridin-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (0.095 g, 60%) as a tan oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give an orange residue
  3. additionwere added to the flask
  4. additioncontaining the orange residue
  5. stirringthe resulting mixture was stirred at 50° C. for 12 hours
  6. customStandard basic workup gave the crude product as an orange oil
  7. customPurification by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 93:5:2, v/v/v)

Sources & evidence

ORD record
ord-952f82dd213e48b7ad8145e06c67978c
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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