Oxalyl chloride → HCID 57876395, compound

HRID 1465292Notes

Reaction equation

HRID 1465292 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([OH:14])=O)[C:6]3[CH2:15][CH2:16][N:17]([CH3:19])[CH2:18][C:5]=3[C:4]=2[CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:26]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:28])[CH3:27]>ClCCl>[C:26]([N:29]1[CH2:34][CH2:33][N:32]([C:12](=[O:14])[CH2:11][N:7]2[C:8]3[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=3[C:5]3[CH2:18][N:17]([CH3:19])[CH2:16][CH2:15][C:6]2=3)[CH2:31][CH2:30]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 837951-AcetylpiperazineHCID 59161636HCID 59161636, compound

Product 1

HCID 57876395HCID 57876395, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetic acid (125 mg, 0.45 mmol) and oxalyl chloride (2 ml) in dichloromethane (6.0 ml) was stirred at 25 deg C. for 3 h. The reaction mixture was concentrated to dryness. The resulting crude was dissolved in dichloromethane (6.0 ml) and DMAP (64 mg, 052 mmol) was added followed by addition of acetyl piperazine (56 mg, 0.43 mmol). The resulting mixture was stirred at 25 deg C. for 14 h. The solvent was removed in vacuo and purified by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL) to obtain 20 mg of 1-(4-Acetyl-piperazin-1-yl)-2-(8-chloro-2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-ethanone as trifluoroacetic acid salt.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionThe resulting crude was dissolved in dichloromethane (6.0 ml)
  3. additionDMAP (64 mg, 052 mmol) was added
  4. stirringThe resulting mixture was stirred at 25 deg C
  5. waitfor 14 h
  6. customThe solvent was removed in vacuo
  7. custompurified by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL)

Sources & evidence

ORD record
ord-ef8df5fc91764f6b8f6b7f8b5a0dfe09
Source dataset
uspto-grants-2015_04
Patent number
US08999978B2

Reaction notes

Loading…