2-Methanesulfonylacetic acid → Methyl 2-(4-((N-(3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-2-(methylsulfonyl)acetamido)methyl)phenyl)acetate

HRID 2090261Notes

Reaction equation

HRID 2090261 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][CH2:33][CH3:34])[N:14]([CH2:15][CH2:16][CH2:17][NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][CH:21]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[CH3:35][S:36]([CH2:39][C:40](O)=[O:41])(=[O:38])=[O:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][CH2:33][CH3:34])[N:14]([CH2:15][CH2:16][CH2:17][N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:25]=3)[C:40](=[O:41])[CH2:39][S:36]([CH3:35])(=[O:38])=[O:37])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 37328412-Methanesulfonylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 25106601Methyl 2-(4-((3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

Product 1

HCID 25106777Methyl 2-(4-((N-(3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-2-(methylsulfonyl)acetamido)methyl)phenyl)acetateYield 43.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from example 1 (221 mg) in DCM (10 mL) was added 2-(methylsulfonyl)acetic acid (66.4 mg) followed by TEA (0.201 mL) and HATU (201 mg). The reaction mixture was stirred at rt for 16 h then the solvents were evaporated. The crude product was purified by RPHPLC to afford the title compound (120 mg) as a white solid.

Workup

  1. customthe solvents were evaporated
  2. customThe crude product was purified by RPHPLC

Sources & evidence

ORD record
ord-290f78c7b34c42f68a0a10e1cfb90e94
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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