1-methyl-1H-imidazole-4-sulfonyl chloride → Methyl 2-(3-((N-(3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propyl)-1-methyl-1H-imidazole-4-sulfonamido)methyl)phenyl)acetate

HRID 2387783Notes

Reaction equation

HRID 2387783 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:15]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=2)=[C:4]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:3]=1.[CH3:31][N:32]1[CH:36]=[C:35]([S:37](Cl)(=[O:39])=[O:38])[N:34]=[CH:33]1>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][CH2:10][CH2:11][N:12]([CH2:13][C:14]2[CH:15]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=2)[S:37]([C:35]2[N:34]=[CH:33][N:32]([CH3:31])[CH:36]=2)(=[O:39])=[O:38])=[C:4]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:3]=1

Participants

4

Reactant 2

HCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 42613957Methyl 2-(3-((3-(2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenyl)acetate

Product 1

HCID 42612990Methyl 2-(3-((N-(3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propyl)-1-methyl-1H-imidazole-4-sulfonamido)methyl)phenyl)acetateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from Example 1 (80 mg) dissolved in DCM (5 mL) was added 1-methylimidazole-4-sulfonyl chloride (38.4 mg) and TEA (0.032 mL) under nitrogen. The resulting solution was stirred at rt for 16 h, the solvents were evaporated and the residue redissolved in MeOH and the crude product purified by RPHPLC to afford the title compound 69 mg.

Workup

  1. customthe solvents were evaporated
  2. dissolutionthe residue redissolved in MeOH
  3. customthe crude product purified by RPHPLC

Sources & evidence

ORD record
ord-e20f0f2401af4128932f2469ec4dda1f
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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