Chlorosuccinimide → HCID 45274281, compound

HRID 1622395Notes

Reaction equation

HRID 1622395 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1.[Cl:17]N1C(=O)CCC1=O.ClC1C=NC=C(Cl)C=1N1CCC(C(N)=O)CC1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:17])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 28116401-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamideHCID 45275354HCID 45275354, compound

Product 1

HCID 45274281HCID 45274281, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide E36 (100 mg, 0.35 mmol) in DMF (7.00 mL) was added N-chlorosuccinimide (94 mg, 0.70 mmol). The reaction was heated to 80° C. and stirred for 8 hours before partitioning between EtOAc and water (100 ml each), the separated organic layer was washed with water (2×75 ml), brine (20 mL), dried (MgSO4) and concentrated under reduced pressure to give a crude clear pale yellow oil (82 mg). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 98:2-84:16, biotage 25+S) followed by flash column chromatography on silica gel (CH2Cl2, EtOH, 96:4-82:18, biotage 14+M) to give a mixture of title compound and 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide by-product as a white solid (20 mg). The mixture was further purified by preparative hplc (MeOH, H2O, 9:20, 25 min) to furnish the title compound as a white solid, LC-MS (ESI, 4 min) Rt 2.46 min, m/z 320 (100%, [M+H]+); m/z (ESI) C11H13N3OClBr requires 316.9931, found [M+H]+ 318.0003.

Workup

  1. custombefore partitioning between EtOAc and water (100 ml each)
  2. washthe separated organic layer was washed with water (2×75 ml), brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a crude clear pale yellow oil (82 mg)
  6. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 98:2-84:16, biotage 25+S)
  7. customto give

Sources & evidence

ORD record
ord-7c2c2537c2ce40c89e2f36c07fe8655e
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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