Mono-Methyl Succinate → Methyl 4-((3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propyl)(3-(2-methoxy-2-oxoethyl)benzyl)amino)-4-oxobutanoate

HRID 2387780Notes

Reaction equation

HRID 2387780 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.[C:31]([O:38][CH3:39])(=[O:37])[CH2:32][CH2:33][C:34]([O-])=[O:35].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[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][CH2:10][CH2:11][N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:15]=2)[C:34](=[O:35])[CH2:33][CH2:32][C:31]([O:38][CH3:39])=[O:37])=[C:4]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:3]=1

Participants

5

Reactant 3

HCID 6930703Mono-Methyl SuccinateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 42613957Methyl 2-(3-((3-(2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenyl)acetate

Product 1

HCID 57824839Methyl 4-((3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propyl)(3-(2-methoxy-2-oxoethyl)benzyl)amino)-4-oxobutanoateYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 1 (61 mg), mono-methyl succinate (23.4 mg) and TEA (0.062 ml) were dissolved in DCM (15 ml) then HATU (61.7 mg) was added. The resulting solution was stirred at rt for 16 h. The solvents were evaporated, the residue was taken up in MeOH and the crude product was purified by RPHPLC to afford the title compound as a colorless gum 32 mg.

Workup

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

Sources & evidence

ORD record
ord-420790d3aa5045e2ab51d976ff458f55
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

Loading…