Valeryl chloride → HCID 22344433, compound

HRID 2090230Notes

Reaction equation

HRID 2090230 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[NH2:22])([CH3:4])([CH3:3])[CH3:2].[C:24](Cl)(=O)[CH2:25][CH2:26][CH2:27][CH3:28]>CN1C(=O)CCC1>[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=[C:24]1[CH2:25][CH2:26][CH2:27][CH3:28])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 61186Valeryl chlorideHCID 66958404HCID 66958404, compound

Product 1

HCID 22344433HCID 22344433, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The product from step (iii) (1.23 g) was dissolved in NMP (25 mL) and valeryl chloride (0.46 mL) was added dropwise. The reaction mixture was stirred for 1.5 h at rt, heated to 50° C. for 24 h then heated to 80° C. for 2 days. The solvent was evaporated and the reaction mixture poured into DCM. The solid precipitate was filtered off and the filtrate was purified on silica eluting with 10% MeOH in DCM to give subtitle compound (0.9 g).

Workup

  1. temperatureheated to 50° C. for 24 h
  2. temperaturethen heated to 80° C. for 2 days
  3. customThe solvent was evaporated
  4. additionthe reaction mixture poured into DCM
  5. filtrationThe solid precipitate was filtered off
  6. customthe filtrate was purified on silica eluting with 10% MeOH in DCM

Sources & evidence

ORD record
ord-8f99313db4284f1e9b11195141d52ddd
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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