Chlorosuccinimide → HCID 86724448, compound

HRID 870958Notes

Reaction equation

HRID 870958 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:18]3[CH:17]=[CH:16][C:15]([O:19][CH2:20][C@@H:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:14][C:13]=3[O:12][CH2:11][C:8]2=[CH:9][N:10]=1)(=[O:3])[CH3:2].C1C(=O)N([Cl:41])C(=O)C1>C(#N)C>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:18]3[CH:17]=[C:16]([Cl:41])[C:15]([O:19][CH2:20][C@@H:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:14][C:13]=3[O:12][CH2:11][C:8]2=[CH:9][N:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86724449HCID 86724449, compound

Product 1

HCID 86724448HCID 86724448, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The stirred solution of (S)-tert-butyl (1-((2-acetamido-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (100 mg, 0.220 mmol) (prepared as described in Example 18, Part H) and NCS (29.3 mg, 0.220 mmol) in acetonitrile (15 mL) was heated to 80° C. for 12 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between water (25 mL) and DCM (25 mL). The organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford (S)-tert-butyl (1-((2-acetamido-9-chloro-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (120 mg, 0.174 mmol, 79% yield) as an off-white solid. The product was used as is for the next step without purification. LCMS (ESI) m/e 490.2 [(M+H)+, calcd for C25H33ClN3O5 490.2]; LC/MS retention time (Method D): tR=1.98 min.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between water (25 mL) and DCM (25 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2901dea3cc1d4d7185c58d80e711d00c
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

Loading…