Dimethylformamide → HCID 57635097, compound

HRID 535942Notes

Reaction equation

HRID 535942 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[C@H:3]([NH:7][C:8]([C:10]1[N:11]=[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:14]=12)=[O:9])[C:4](O)=[O:5].C(Cl)(=O)C([Cl:31])=O.CN(C=O)C>C(Cl)Cl>[CH3:1][C:2]([CH3:27])([CH3:26])[C@H:3]([NH:7][C:8]([C:10]1[N:11]=[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:14]=12)=[O:9])[C:4]([Cl:31])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 57635153HCID 57635153, compound2×

Product 1

HCID 57635097HCID 57635097, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (S)-3,3-dimethyl-2-(7-methyl-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamido)butanoic acid (Compound 281) (0.11 g, 0.30 mmol) in DCM was added oxalyl chloride (0.08 g, 0.60 mmol) followed by a catalytic amount of DMF. The resulting mixture was stirred for 2 h and the solvent was evaporated, toluene (2 mL) was added and the mixture was concentrated again. The resulting product (Intermediate 23A) was dried under vacuum and then used in the next step without further purification.

Workup

  1. customthe solvent was evaporated
  2. additiontoluene (2 mL) was added
  3. concentrationthe mixture was concentrated again
  4. dry with materialThe resulting product (Intermediate 23A) was dried under vacuum
  5. customused in the next step without further purification

Sources & evidence

ORD record
ord-f9a5fa59e9f54777973c6d22ed0b0bd2
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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