Pyridine → HCID 67040428, compound

HRID 605317Notes

Reaction equation

HRID 605317 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[S:12][C:13]([S:19][C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=3)=[C:14]([N+:16]([O-])=O)[CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.Cl[C:34]([O:36][CH2:37][C:38]([Cl:41])([Cl:40])[Cl:39])=[O:35]>ClCCl>[Cl:39][C:38]([Cl:41])([Cl:40])[CH2:37][O:36][C:34](=[O:35])[NH:26][C:23]1[CH:24]=[CH:25][C:20]([S:19][C:13]2[S:12][C:11]([C:9](=[O:10])[NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)=[CH:15][C:14]=2[NH2:16])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 67040571HCID 67040571, compound

Product 1

HCID 67040428HCID 67040428, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product from Example 356C dissolved in dichloromethane was added pyridine followed by the dropwise addition of 2,2,2-trichloroethyl chloroformate. The resultant solution was stirred for 4 hours and then concentrated under vacuum. The mixture was then poured into water, the pH of the solution adjusted to 5 with 1N aqueous hydrochloric acid, the resultant solution stirred for 30 minutes and the resultant solid collected and dried followed by reduction of the nitro group according to the procedure described in Example 356E to provide the title product.

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe mixture was then poured into water
  3. customthe resultant solid collected
  4. customdried

Sources & evidence

ORD record
ord-8adc72045f2d4c1caf4f55ddfa2667e3
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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