Methanesulfonyl chloride → Methyl 2-(3-((N-(3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propyl)methylsulfonamido)methyl)phenyl)acetate

HRID 1617130Notes

Reaction equation

HRID 1617130 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][S:32](Cl)(=[O:34])=[O:33]>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:32]([CH3:31])(=[O:34])=[O:33])=[C:4]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 42613957Methyl 2-(3-((3-(2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenyl)acetate

Product 1

HCID 42614106Methyl 2-(3-((N-(3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propyl)methylsulfonamido)methyl)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from Example 1 (70 mg) dissolved in DCM was added methanesulfonyl chloride (16 μl) and TEA (28.3 μl) under nitrogen. The resulting solution was stirred at rt for 16 h. The solvents were evaporated, the residue redissolved in MeOH and the crude product was purified by RPHPLC to afford the title compound 32 mg.

Workup

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

Sources & evidence

ORD record
ord-4639d094f4a6453a90f5f7f91ca05bf4
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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