Pyridine → HCID 86725353, compound

HRID 925244Notes

Reaction equation

HRID 925244 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:22][CH2:21][C:10]2[C:11]3[CH:12](O)[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].N1C=CC=CC=1.O=S(Cl)[Cl:31]>>[CH2:1]([O:3][C:4]([N:6]1[CH2:22][CH2:21][C:10]2[C:11]3[CH:12]([Cl:31])[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86725354HCID 86725354, compound

Product 1

HCID 86725353HCID 86725353, compound

Conditions

Temperature
70 °C

Procedure

To a stirred solution of the product from step (a) (25 mg) in SOCl2 (1 ml) was added pyridine (1 ml). The mixture was heated to 70° C. for 30 minutes after which LCMS indicates no starting material. The volatiles were evaporated in vacuo. The residue was dissolved in EtOAc and washed with 1 M citric acid, saturated NaHCO3, brine, dried (Na2SO4), and solvent evaporated in vacuo to give the sub-titled compound (21 mg) as a colorless oil which was used as obtained in the next step. MS: ESI (positive): 330 (M+H).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 1 M citric acid, saturated NaHCO3, brine
  4. dry with materialdried (Na2SO4), and solvent
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3353fb7cf4dd4e8da9e012765d7b3d0b
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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