Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → Methyl 2-(3-((N-(3-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propyl)-3-(dimethylamino)propanamido)methyl)phenyl)acetate
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.Cl.[CH3:32][N:33]([CH3:39])[CH2:34][CH2:35][C:36](O)=[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[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)[C:36](=[O:37])[CH2:35][CH2:34][N:33]([CH3:39])[CH3:32])=[C:4]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:3]=1Participants
5
Reactant 3
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 115863273-(Dimethylamino)propanoic acid hydrochloride
HCID 42613957Methyl 2-(3-((3-(2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenyl)acetateProduct 1
Reagents, catalysts & solvents 1
Procedure
The product from Example 1 (80 mg) and 3-(dimethylamino)propanoic acid hydrochloride (45 mg) were combined in DCM (5 mL) then TEA (73 mg) and HATU (101 mg) were added. The reaction mixture was stirred at rt for 16 h. The solvents were evaporated, the residue dissolved in MeOH and purified by RPHPLC to give the title compound 32 mg.
Workup
- customThe solvents were evaporated
- dissolutionthe residue dissolved in MeOH
- custompurified by RPHPLC
Sources & evidence
- ORD record
- ord-db02f82ec000473d8185cc0005cacc56
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765939B2
Reaction notes
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