2-(Ethylamino)ethanol → N-(4-(8-((Ethyl(2-hydroxyethyl)amino)methyl)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridin-1-ylamino)phenyl)benzamide

HRID 1029232Notes

Reaction equation

HRID 1029232 reaction equation
CCN(C(C)C)C(C)C.CS(Cl)(=O)=O.O[CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][C:28]=3[NH:30][C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:45])[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:33][CH:32]=3)[NH:23][C:22](=[O:46])[C:21]=2[CH:47]=1.[CH2:48]([NH:50][CH2:51][CH2:52][OH:53])[CH3:49]>C(Cl)Cl>[CH2:48]([N:50]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][C:28]=3[NH:30][C:31]3[CH:32]=[CH:33][C:34]([NH:37][C:38](=[O:45])[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:35][CH:36]=3)[NH:23][C:22](=[O:46])[C:21]=2[CH:47]=1)[CH2:51][CH2:52][OH:53])[CH3:49]

Participants

6

Reactant 4

HCID 80722-(Ethylamino)ethanolHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58168103N-(4-(8-(Hydroxymethyl)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridin-1-ylamino)phenyl)benzamide

Product 1

HCID 44205508N-(4-(8-((Ethyl(2-hydroxyethyl)amino)methyl)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridin-1-ylamino)phenyl)benzamideYield 19.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIEA (0.03 mL, 0.19 mmol) and methanesulfonyl chloride (0.01 mL, 0.09 mmol) were added to a solution of 273 (27 mg, 0.06 mmol) in CH2Cl2 and stirred for 2 h at room temperature. 2-(Ethylamino)ethanol (17 mg, 0.19 mmol) was added, and the reaction mixture was stirred for 1 h. The crude product was purified directly via HP-LC to provide 274 (6 mg, 16% yield) as a solid. LC-MS (M+H=508, obsd.=508).

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. customThe crude product was purified directly via HP-LC

Sources & evidence

ORD record
ord-b1ca37c8d9f547c2acc600e1106c33ff
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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