Pyridine → HCID 68532896, compound

HRID 644217Notes

Reaction equation

HRID 644217 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:32]=[C:31]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH:30]=[CH:29][C:16]=2[C:17]([NH:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([OH:24])=O)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.C(Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:32]=[C:31]([N:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)[CH:30]=[CH:29][C:16]=2[C:17]2[O:18][C:22](=[O:24])[C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 68530506HCID 68530506, compound

Product 1

HCID 68532896HCID 68532896, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)-benzoylamino]benzoic acid (about 11.23 mmol) was diluted with methylene chloride (115 mL). DMF (4 drops) and pyridine (1.1 mL, 13.6 mmol) were added, followed by oxalyl chloride (1.1 mL, 12.6 mmol). A precipitate formed immediately. After 2 hours, the reaction was filtered and the filtrate was concentrated in vacuo. The crude residue from the filtrate concentration was purified by flash column chromatography (5% EtOAc/CH2Cl2) to give the desired product (4.83 g, 9.82 mmol, 87%) as a yellow solid.

Workup

  1. customA precipitate formed immediately
  2. filtrationthe reaction was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. concentrationThe crude residue from the filtrate concentration
  5. customwas purified by flash column chromatography (5% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-9511ebe6e54448c3b263f25f018c3da6
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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