Diisopropylethylamine → 3-{[2-(4-amino-furazan-3-yl)-1-phenyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}-N-[2-(4-morpholinyl)ethyl]benzamide

HRID 1986372Notes

Reaction equation

HRID 1986372 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:9]3[CH:14]=[C:13]([O:15][C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19]([OH:21])=O)[N:12]=[CH:11][C:10]=3[N:25]=2)=[N:4][O:5][N:6]=1.C(N(CC)C(C)C)(C)C.[NH2:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>ClCCl>[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:9]3[CH:14]=[C:13]([O:15][C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19]([NH:41][CH2:42][CH2:43][N:44]4[CH2:49][CH2:48][O:47][CH2:46][CH2:45]4)=[O:21])[N:12]=[CH:11][C:10]=3[N:25]=2)=[N:4][O:5][N:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 113159523-{[2-(4-Amino-furazan-3-yl)-1-phenyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}benzoic acid

Product 1

HCID 111684733-{[2-(4-amino-furazan-3-yl)-1-phenyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}-N-[2-(4-morpholinyl)ethyl]benzamideYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Step 9 (0.020 g, 0.048 mmol) in dichloromethane (2 mL) and N,N-diisopropylethylamine (0.02 mL, 0.11 mmol) was treated with N-(2-aminoethyl)morpholine and the PyBoP reagent (2 equiv) and stirred at rt for 2 h. The reaction mixture was concentrated and the residue was purified by reverse phase HPLC to give the compound (0.008 g, 31%). MS (ES+) m/e 527 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c139053b613f49ff93da7b1cea88945a
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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