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Water → 2-Chloro-6-(3-methoxy-1-azetidinyl)-4-[1-(3-oxetanyl)-4-piperidinyl]pyridine

HRID 1778184
Notes
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Reaction equation

HRID 1778184 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH:14]3[CH2:17][O:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:18])[N:3]=1.Cl.[CH3:20][O:21][CH:22]1[CH2:25][NH:24][CH2:23]1.CCN(C(C)C)C(C)C.O>CS(C)=O>[Cl:18][C:4]1[CH:5]=[C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH:14]3[CH2:17][O:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:7]=[C:2]([N:24]2[CH2:25][CH:22]([O:21][CH3:20])[CH2:23]2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 222428583-Methoxyazetidine hydrochlorideHCID 900154092,6-Dichloro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridine

Product 1

HCID 1176783762-Chloro-6-(3-methoxy-1-azetidinyl)-4-[1-(3-oxetanyl)-4-piperidinyl]pyridineYield 60.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,6-dichloro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridine (450 mg, 1.57 mmol), 3-methoxyazetidine hydrochloride (963 mg, 7.83 mmol) and DIPEA (3 mL, 16.9 mmol) in DMSO (5 mL) was stirred at 100° C. for 16 h. The mixture was poured into water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, evaporated and purified by flash column chromatography on silica gel (30% ethyl acetate in petroleum ether) to give 2-chloro-6-(3-methoxyazetidin-1-yl)-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridine (320 mg, 60.3% yield). LCMS (ESI) [MH]+=337.8

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. custompurified by flash column chromatography on silica gel (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-5ab329c9e2f7463aadf949b8d7089685
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266862B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes