Pyridine → HCID 178472407, compound

HRID 2202747Notes

Reaction equation

HRID 2202747 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9](=[O:43])[CH2:10][N:11]([CH2:34][C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([F:42])[CH:36]=1)[C:12]([C:14]1[CH:15]=[N:16][N:17]([C@H:23]2[CH2:28][CH2:27][C@H:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]2)[C:18]=1[C:19]([F:22])([F:21])[F:20])=[O:13].N1C=CC=CC=1.[CH3:50][C:51](Cl)=[O:52]>C(Cl)Cl>[C:51]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9](=[O:43])[CH2:10][N:11]([CH2:34][C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([F:42])[CH:36]=1)[C:12]([C:14]1[CH:15]=[N:16][N:17]([C@H:23]2[CH2:28][CH2:27][C@H:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]2)[C:18]=1[C:19]([F:22])([F:21])[F:20])=[O:13])(=[O:52])[CH3:50]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 178472417HCID 178472417, compound

Product 1

HCID 178472407HCID 178472407, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 11-3 (45 mg, 0.07 mmol) in 1:1 mixture of pyridine and DCM (5 mL) was added CH3COCl (6 μL, 0.08 mmol) at 0° C. and stirred for 2 h. The reaction mixture was quenched with water (20 mL) and extracted with DCM (2×10 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent) to provide compound 13-1 (50 mg, quant.) as a yellow solid.

Workup

  1. customThe reaction mixture was quenched with water (20 mL)
  2. extractionextracted with DCM (2×10 mL)
  3. washThe combined organic layers were washed with water (50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent)

Sources & evidence

ORD record
ord-04e5733a46a34e918cb25c1a57a943af
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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