Trifluoroacetic acid → (4-{[[3-(6-Amino-2-butoxy-8-oxo-7,8-dihydro-purin-9-yl)-propyl]-(3-piperazin-1-yl-propionyl)-amino]-methyl}-phenyl)-acetic acid methyl ester

HRID 1095339Notes

Reaction equation

HRID 1095339 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][N:16]2[C:24](=[O:25])[NH:23][C:22]3[C:17]2=[N:18][C:19]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[N:20][C:21]=3[NH2:26])=[CH:7][CH:6]=1.C(OC([N:40]1[CH2:45][CH2:44][N:43]([CH2:46][CH2:47][C:48](O)=[O:49])[CH2:42][CH2:41]1)=O)(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH2:13][CH2:14][CH2:15][N:16]2[C:24](=[O:25])[NH:23][C:22]3[C:17]2=[N:18][C:19]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[N:20][C:21]=3[NH2:26])[C:48](=[O:49])[CH2:47][CH2:46][N:43]2[CH2:44][CH2:45][NH:40][CH2:41][CH2:42]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 27356443-(1-TERT-BUTOXYCARBONYLPIPERAZIN-4-YL)PROPIONIC ACIDHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90697362Methyl[4-({[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl]amino}methyl)phenyl]acetate

Product 1

HCID 24962786(4-{[[3-(6-Amino-2-butoxy-8-oxo-7,8-dihydro-purin-9-yl)-propyl]-(3-piperazin-1-yl-propionyl)-amino]-methyl}-phenyl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of example 1, step (ix) (0.27 g) was dissolved in DCM (10 ml) and treated with 4-(2-carboxy-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (0.16 g) and HATU (0.23 g). The reaction was stirred at rt for 16 h, before 2 mls of TFA added. The mixture was purified by RPHPLC, to give the title compound. Yield 3 mg.

Workup

  1. additionadded
  2. customThe mixture was purified by RPHPLC

Sources & evidence

ORD record
ord-05b8fa2dfc674d9fb1ee7aa3510afcc3
Source dataset
uspto-grants-2012_03
Patent number
US08138172B2

Reaction notes

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