Pyridine → HCID 470762, compound

HRID 724937Notes

Reaction equation

HRID 724937 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:29]=[N:28][C:13]3[N:14]([CH2:26][CH3:27])[C:15]4[N:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:16]=4[N:17]([CH3:20])[C:18](=[O:19])[C:12]=3[CH:11]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[Cl:25][C:23]1[CH:22]=[CH:21][C:16]2[N:17]([CH3:20])[C:18](=[O:19])[C:12]3[CH:11]=[C:10]([CH2:9][CH2:8][C:5]4[CH:6]=[CH:7][C:2]([NH:1][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:3][CH:4]=4)[CH:29]=[N:28][C:13]=3[N:14]([CH2:26][CH3:27])[C:15]=2[N:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 470756HCID 470756, compound

Product 1

HCID 470762HCID 470762, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-[2-(4-aminophenyl)ethyl]-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (16 mg, 0.04 mmol) and 6 μL of pyridine in dichloromethane at 0° C. was added 5 μL of methanesulfonyl chloride. The reaction mixture was allowed to stir at room temperature overnight. The orange reaction mixture was then concentrated to dryness and the product was purified by flash chromatography, eluting with methanol/dichloromethane, and recrystallization from ethanol/hexanes to give 6 mg of the title compound, m.p. 199°-204° C.

Workup

  1. concentrationThe orange reaction mixture was then concentrated to dryness
  2. customthe product was purified by flash chromatography
  3. washeluting with methanol/dichloromethane, and recrystallization from ethanol/hexanes

Sources & evidence

ORD record
ord-4d3775dedeea4ad0926406d9a264fbe8
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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