Triethylamine → HCID 66680346, compound

HRID 1626745Notes

Reaction equation

HRID 1626745 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([OH:15])=O)[CH:8]=1.Cl.[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([NH:34][C:35]([CH:37]2[CH2:42][CH2:41][CH2:40][NH:39][CH2:38]2)=[O:36])=[C:28]([CH:33]=1)[C:29]([O:31][CH3:32])=[O:30].C(N(CC)CC)C.O.C(=O)(O)[O-].[Na+]>CC(N(C)C)=O.C1COCC1.CN(C=O)C>[C:7]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([N:39]2[CH2:40][CH2:41][CH2:42][CH:37]([C:35]([NH:34][C:27]3[CH:26]=[CH:25][C:24]([Cl:23])=[CH:33][C:28]=3[C:29]([O:31][CH3:32])=[O:30])=[O:36])[CH2:38]2)=[O:15])[CH:8]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 65578Oxalyl chlorideHCID 66680551HCID 66680551, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66680346HCID 66680346, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

A catalytic amount of DMF and 114 mg (0.900 mmol) of oxalyl chloride were added at 0° C. to 2 mL of THF solution comprising 119 mg (0.600 mmol) of biphenyl-3-carboxylic acid, and the mixture was stirred at room temperature for 40 minutes. The solvent was distilled off under reduced pressure, and then 2 mL of DMAc, 200 mg (0.600 mmol) of the methyl 5-chloro-2-[(piperidin-3-ylcarbonyl)amino]benzoate hydrochloride obtained in Example 11-(ii), and 0.092 mL (0.660 mmol) of triethylamine were added in this order to the residue at 0° C., and the mixture was stirred for 3 hours. After the completion of the reaction, saturated sodium bicarbonate water was added under ice-cooling, and the mixture was stirred. The resulting solids were collected by filtration, washed with water, and dried under reduced pressure at 50° C. for 3 hours, thereby giving 270 mg of methyl 2-({[1-(biphenyl-3-ylcarbonyl)piperidin-3-yl]carbonyl}amino)-5-chlorobenzoate (yield: 94%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. stirringthe mixture was stirred for 3 hours
  3. additionwas added under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred
  6. filtrationThe resulting solids were collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure at 50° C. for 3 hours

Sources & evidence

ORD record
ord-7a61edc97a274786903ed29de8e31d8a
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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