Pyridine → HCID 59623756, compound

HRID 1093948Notes

Reaction equation

HRID 1093948 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[S:11](=[O:22])(=[O:21])[NH:12][C:13]2[C:18]([C:19]=1[OH:20])=[N:17][CH:16]=[CH:15][N:14]=2.N1C=CC=CC=1.[CH3:29][C:30]([CH3:35])([CH3:34])[C:31](Cl)=[O:32]>ClCCl>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[S:11](=[O:21])(=[O:22])[NH:12][C:13]2[C:18]([C:19]=1[O:20][C:31](=[O:32])[C:30]([CH3:35])([CH3:34])[CH3:29])=[N:17][CH:16]=[CH:15][N:14]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 59623744HCID 59623744, compound

Product 1

HCID 59623756HCID 59623756, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of Compound No. A2 (Example 3.1) in dichloromethane (10 ml) was added pyridine (0.205 ml) followed by 2,2-dimethylpropionyl chloride (0.15 ml). The reaction mixture was heated to 40° C. for 4 hours and then stored at ambient temperature of 16 hours. The reaction mixture was partition between dichloromethane (30 ml) and aqueous hydrochloric acid (2M) (30 ml). The phases were separated. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were concentrated. The residue was triturated with iso-hexane and dried under vacuum to give Compound No. B3 of Table B (408 mg) as a yellow solid.

Workup

  1. additionTo a suspension of Compound No
  2. customThe reaction mixture was partition between dichloromethane (30 ml) and aqueous hydrochloric acid (2M) (30 ml)
  3. customThe phases were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. concentrationThe combined organic extracts were concentrated
  6. customThe residue was triturated with iso-hexane
  7. customdried under vacuum
  8. customto give Compound No

Sources & evidence

ORD record
ord-f719d410aef34e9fb96655d53d181f2b
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

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