Pyridine → HCID 58181659, compound

HRID 237314Notes

Reaction equation

HRID 237314 reaction equation
[OH:1][C@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C:11]1=[O:26])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:27][C:28](OC(C)=O)=[O:29].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:28]([O:1][C@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:18][CH:17]=2)[C:11]1=[O:26])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])(=[O:29])[CH3:27]

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 58181382HCID 58181382, compound

Product 1

HCID 58181659HCID 58181659, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Compound 93-1 (350 mg, 0.932 mmol) was dissolved in CH2Cl2 (4.66 ml) and cooled to 0° C., Ac2O (0.176 ml, 2 eq), pyridine (0.151 ml, 2 eq), and DMAP (11 mg, 0.1 eq) was added. The mixture was stirred for 2 hours, diluted with EtOAc, washed with CuSO4 solution, water, dried and concentrated to give 370 mg of compound 93-2.

Workup

  1. washwashed with CuSO4 solution, water
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5098cfe2de234066a55e2d94c9a52937
Source dataset
uspto-grants-2014_02
Patent number
US08642582B2

Reaction notes

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