Triethylamine → HCID 12083053, compound

HRID 1168528Notes

Reaction equation

HRID 1168528 reaction equation
Br[CH2:2][C:3](OC(=O)CBr)=[O:4].[CH2:10]([NH:17][CH2:18][C:19]1[CH:20]=[C:21]([CH2:41][N:42]2[CH2:47][CH2:46][O:45][CH2:44][CH2:43]2)[CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][C:25]([C:29]([NH:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)=[O:30])=[C:24]2[OH:40])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>CN1C(=O)CCC1.O>[CH2:10]([N:17]1[CH2:18][C:19]2=[C:28]3[C:23](=[CH:22][C:21]([CH2:41][N:42]4[CH2:43][CH2:44][O:45][CH2:46][CH2:47]4)=[CH:20]2)[C:24](=[O:40])[C:25]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)=[O:30])=[CH:26][N:27]3[CH2:2][C:3]1=[O:4])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4259817Bromoacetic anhydrideHCID 178522895HCID 178522895, compound

Product 1

HCID 12083053HCID 12083053, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Bromoacetic anhydride (40 mg) is added to a stirred solution of 8-((benzylamino)methyl)-N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (Preparation 29, 53 mg) in NMP (0.3 mL). After 30 min, triethylamine (50 mg) is added. The solution is diluted with water and the resulting precipitate is filtered and dried under vacuum to give 44 mg of the title compound. Physical characteristics: HRMS m/z 571.2104 (C32H31ClN4O4).

Workup

  1. filtrationthe resulting precipitate is filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-c2eff30fa81c4194a5a9e924dddf1432
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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