Methanol → Methyl 2-(4-((N-(3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-3-(piperidin-1-yl)propanamido)methyl)phenyl)acetate

HRID 2090267Notes

Reaction equation

HRID 2090267 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][O: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.[N:35]1([CH2:41][CH2:42][C:43](O)=[O:44])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CO>CN(C=O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][O: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:43](=[O:44])[CH2:42][CH2:41][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1177821-Piperidinepropanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68430910Methyl 2-(4-((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

Product 1

HCID 25107147Methyl 2-(4-((N-(3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-3-(piperidin-1-yl)propanamido)methyl)phenyl)acetateYield 11.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the product from step (v) of example 29 (480 mg, 1.04 mmol) in DMF (5 mL), 3-(piperidin-1-yl)propanoic acid (196 mg, 1.25 mmol) and HATU (475 mg, 1.25 mmol) were added at rt and stirred for 2 hours. After adding 1 mL of methanol, the crude product was purified by RPHPLC and the resulting residue was triturated with diethyl ether: EtOAc (5:1). The suspension was filtered to afford the title compound as a white solid (72 mg).

Workup

  1. customthe crude product was purified by RPHPLC
  2. customthe resulting residue was triturated with diethyl ether: EtOAc (5:1)
  3. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-e38ab1a51ad846b68ddea09f89c0491a
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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