Chlorosuccinimide → HCID 86706743, compound

HRID 710031Notes

Reaction equation

HRID 710031 reaction equation
[OH:1][N:2]=[CH:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1C(=O)N(Cl)C(=O)C1.[CH2:24]([O:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[C:25]#[CH:26].C(=O)(O)[O-].[Na+]>C1COCC1.CCN(CC)CC.CN(C=O)C>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([O:27][CH2:24][C:25]2[O:1][N:2]=[C:3]([C@@H:4]3[CH2:8][CH2:7][CH2:6][N:5]3[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:26]=2)[CH:29]=1

Participants

8

Reactant 4

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 114236223-(Prop-2-ynyloxy)pyridineHCID 86706742HCID 86706742, compound

Product 1

HCID 86706743HCID 86706743, compoundYield 55.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a DMF (60 mL) solution of the compound (8.57 g) obtained in Example 2-(1), NCS (5.341 g) was added in small portions at 0° C. and the mixture was stirred at room temperature for an hour. The reaction mixture was cooled to 0° C. and after adding a solution of 3-(prop-2-yn-1-yloxy)pyridine (2.663 g) in THF (5 mL) and a solution of Et3N (5.6 mL) in THF (15 mL), the resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was added to saturated aqueous sodium bicarbonate (200 mL), followed by extraction with AcOEt (200 mL). The resulting organic layer was washed with brine (200 mL), dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (3.81 g, pale yellow solid.)

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionfollowed by extraction with AcOEt (200 mL)
  3. washThe resulting organic layer was washed with brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas further purified by neutral silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-eb8e1c3588984a42b6af5122cccf4046
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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