Pyridine → HCID 67222737, compound

HRID 1968902Notes

Reaction equation

HRID 1968902 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][N:27]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[N:28]1.N1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:18]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:32]([C:29]3[CH:30]=[CH:31][N:27]([CH3:26])[N:28]=3)(=[O:34])=[O:33])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 134744661-Methyl-1H-pyrazole-3-sulfonyl chlorideHCID 672228296-Benzylamino-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 67222737HCID 67222737, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-Benzylamino-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (320 mg, 0.95 mmol), methyl-1-H-pyrazole-3-sulfonyl chloride (303 mg, 1.68 mmol) and pyridine (229 μl, 2.84 mmol) in dry dichloromethane (10 ml) were heated to reflux for 15 hrs. The reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was purified by column chromatography (1% methanol in dichloromethane) to afford the title compound as an off yellow solid (393 mg, 86% yield). HPLC retention time 4.72 min. Mass spectrum (ES+) m/z 505 (M+23, sodium salt).

Workup

  1. temperatureto reflux for 15 hrs
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by column chromatography (1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0180fad137a24b5ab653a78166f0a440
Source dataset
uspto-grants-2013_04
Patent number
US08426442B2

Reaction notes

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