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 1617128Notes

Reaction equation

HRID 1617128 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-61bac1439eba459d9eeae7a2fb343a08
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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