Pyridine → HCID 42600050, compound

HRID 875267Notes

Reaction equation

HRID 875267 reaction equation
[OH:1][C:2]12[CH2:35][CH2:34][C@:33]3([CH3:36])[C:28](=[C:29]([CH3:37])[CH2:30][CH2:31][CH2:32]3)[C@@H:3]1[O:4][C:5](=[O:27])[CH:6]2[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[C:16]=2[CH2:25][OH:26])[CH2:10][CH2:9]1.[C:38](OC(=O)C)(=[O:40])[CH3:39].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[C:38]([O:26][CH2:25][C:16]1[C:17]([O:23][CH3:24])=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:15]=1[CH2:14][N:11]1[CH2:12][CH2:13][N:8]([CH2:7][CH:6]2[C:5](=[O:27])[O:4][C@H:3]3[C:28]4[C@@:33]([CH3:36])([CH2:34][CH2:35][C:2]23[OH:1])[CH2:32][CH2:31][CH2:30][C:29]=4[CH3:37])[CH2:9][CH2:10]1)(=[O:40])[CH3:39]

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 42599806HCID 42599806, compound

Product 1

HCID 42600050HCID 42600050, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Compound of example 38 (200.0 mg, 0.39 mmol) was dissolved in DCM (10 mL). To it was added acetic anhydride (43.86 mg, 0.43 mmol), pyridine (61.70 mg, 0.78 mmol) and DMAP (2 mg) and reaction mixture was stirred at room temperature (25° C.) for 2 hours. Reaction mixture was diluted with water and extracted with DCM (3×50 mL). The crude product was purified by column chromatography (silica gel, 40% ethyl acetate in petroleum ether) to obtain the title compound.

Workup

  1. additionTo it was added
  2. customReaction mixture
  3. extractionextracted with DCM (3×50 mL)
  4. customThe crude product was purified by column chromatography (silica gel, 40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-0e190e8ba63c4dea8f3184cdd7d570ce
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

Loading…