Hydrochloric Acid → HCID 67342233, compound

HRID 1673536Notes

Reaction equation

HRID 1673536 reaction equation
C(Cl)(=O)C(Cl)=O.[N:7]1([C:12]2[N:17]=[CH:16][C:15]([C:18]([OH:20])=O)=[CH:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8]1.[NH2:21][C:22]1[CH:34]=[C:33]([CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:32]=[CH:31][C:23]=1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].Cl>C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[CH2:35]([C:33]1[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[C:22]([NH:21][C:18]([C:15]2[CH:16]=[N:17][C:12]([N:7]3[CH:8]=[CH:9][CH:10]=[CH:11]3)=[CH:13][CH:14]=2)=[O:20])[CH:34]=1)[CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 27641006-(1H-Pyrrol-1-yl)nicotinic acidHCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

Product 1

HCID 67342233HCID 67342233, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.015 mL of N,N-dimethylformamide was added to a mixed solution of 2.0 mL of methylene chloride and 0.024 mL of oxalyl chloride containing 47 mg of 6-(1H-pyrrol-1-yl)pyridine-3-carboxylic acid and stirred at room temperature for 30 minutes. 74 mg of tert-butyl 2-amino-4-phenethylbenzoate and 0.090 mL of triethylamine were added to the reaction mixture at room temperature sequentially and stirred at the same temperature for 1 hour and 40 minutes. 1.0 mol/L hydrochloric acid and ethyl acetate were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform] to obtain 62 mg of tert-butyl 4-phenethyl-2-(6-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoate as white solid.

Workup

  1. stirringstirred at the same temperature for 1 hour and 40 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with a saturated sodium chloride aqueous solution
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform]

Sources & evidence

ORD record
ord-c36689a1578b4a7ab55552ae6145da93
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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