Pyridine → HCID 68292779, compound

HRID 1841991Notes

Reaction equation

HRID 1841991 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11]1[CH:24]=[CH:23][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1.[Cl:25][CH2:26][CH2:27][CH2:28][S:29](Cl)(=[O:31])=[O:30].N1C=CC=CC=1>C1COCC1.C([O-])(O)=O.[Na+]>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([NH:22][S:29]([CH2:28][CH2:27][CH2:26][Cl:25])(=[O:31])=[O:30])[CH2:20][CH2:21]2)=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chlorideHCID 68292563HCID 68292563, compound

Product 1

HCID 68292779HCID 68292779, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of compound 217 (535 mg, 1.65 mmol) in THF (10 mL) is added 3-chloro-propane-1-sulfonyl chloride (0.40 mL, 3.3 mmol) and pyridine (0.27 mL). After 18 h, the mixture is diluted with saturated NaHCO3 and extracted with EtOAc. The organic layer is dried over Na2SO4, filtered, and concentrated. The residue is purified by flash chromatography eluting with a gradient of 0-10% MeOH in DCM to provide 3-chloro-propane-1-sulfonic acid {1-[(S)-4-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-piperidin-4-yl}-amide. LC/MS method 1: ES+ m/z 465.2 [M]+, Rt=0.68 min).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography
  6. washeluting with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-fd32adeb2886435da3cb7182046036fa
Source dataset
uspto-grants-2015_02
Patent number
US08946203B2

Reaction notes

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