Pyridine → HCID 20162879, compound

HRID 246864Notes

Reaction equation

HRID 246864 reaction equation
[NH2:1][C:2]1([NH:7][C:8](=[O:28])[CH:9]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[CH2:5][NH:4][C:3]1=[O:6].N1C=CC=CC=1.[C:35](OC=O)(=[O:37])C>ClCCl>[CH:35]([NH:1][C:2]1([NH:7][C:8](=[O:28])[CH:9]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[CH2:5][NH:4][C:3]1=[O:6])=[O:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 75269Acetic-formic anhydrideHCID 20162869HCID 20162869, compound

Product 1

HCID 20162879HCID 20162879, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The amine (42) (490 mg) in dry dichloromethane was cooled to 0° C. and treated with pyridine (211 mg) followed by formic-acetic anhydride (117 mg). The mixture was stirred at 0° C. for 5 minutes then allowed to warm to room temperature. After 1/2 hour the solvent was evaporated and the residue dried in vacuo. The solid was triturated with dry ether, filtered off, and washed with more ether before drying in vacuo to give the product (43) (510 mg) as a white solid. νmax (NUJOL) 3250 br, 1780sh, 1760, 1680sh, 1655 and 1345 cm-1.

Workup

  1. temperatureto warm to room temperature
  2. customAfter 1/2 hour the solvent was evaporated
  3. customthe residue dried in vacuo
  4. customThe solid was triturated with dry ether
  5. filtrationfiltered off
  6. washwashed with more ether
  7. custombefore drying in vacuo

Sources & evidence

ORD record
ord-2972856175984c719f434c1d1c39e2c2
Source dataset
uspto-grants-1987_11
Patent number
US04704385

Reaction notes

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