Pyridine → HCID 58333439, compound

HRID 2066898Notes

Reaction equation

HRID 2066898 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][N:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:16]=3[F:25])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl.N1CCCCC1>C(Cl)Cl.CO>[N:26]1([C:33]([N:1]2[CH2:6][CH2:5][CH:4]([O:7][N:8]=[C:9]3[CH2:14][CH2:13][N:12]([C:15]4[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:17][C:16]=4[F:25])[CH2:11][CH2:10]3)[CH2:3][CH2:2]2)=[O:35])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8082PiperidineHCID 94429TriphosgeneHCID 866550221-(2-Fluoro-4-methanesulfonyl-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime

Product 1

HCID 58333439HCID 58333439, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 63a (135 mg, 0.35 mmol) and pyridine (85 μL, 1.05 mmol) in DCM (5 mL) was added to a solution of triphosgene (37 mg, 0.123 mmol) in DCM (6 mL) and stirred at r.t. for 1 h. 0.5 mL of this solution was transferred to a vial, piperidine (0.01 mL) was added and the mixture stirred at r.t. for 2 h, diluted with methanol and purified by HPLC yielding 73-1. LC-MS 481.4 (MH+).

Workup

  1. additionwas added
  2. stirringthe mixture stirred at r.t. for 2 h
  3. custompurified by HPLC
  4. customyielding 73-1

Sources & evidence

ORD record
ord-3c9c5e81cf3c4cae971d8a0323fa0458
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

Loading…