1,1'-Carbonyldiimidazole → HCID 10187735, compound

HRID 1168527Notes

Reaction equation

HRID 1168527 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([NH:20][CH2:21][C:22]1[CH:23]=[C:24]([CH2:44][N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)[CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][C:28]([C:32]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)=[O:33])=[C:27]2[OH:43])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN1C(=O)CCC1>[CH2:13]([N:20]1[CH2:21][C:22]2[C:31]3=[C:26]([C:27](=[O:43])[C:28]([C:32]([NH:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=4)=[O:33])=[CH:29][N:30]3[C:1]1=[O:2])[CH:25]=[C:24]([CH2:44][N:45]1[CH2:46][CH2:47][O:48][CH2:49][CH2:50]1)[CH:23]=2)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178522895HCID 178522895, compound

Product 1

HCID 10187735HCID 10187735, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of 1,1′-carbonyldiimidazole (82 mg) in NMP (2.0 mL) is added over 15 min to a solution of 8-((benzylamino)methyl)-N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (Preparation 29, 106 mg) in NMP (6 mL). After an additional 15 min, the solvent is removed under reduced pressure and the residual solid is triturated with methanol to afford 93 mg of the title compound. Physical characteristics: M.p. 201-204° C.; 1H NMR (CDCl3) δ2.44, 3.58, 3.70, 4.67, 4.73, 4.87, 7.3-7.45, 7.51, 8.19, 9.90, 10.1; Anal. Found: C, 66.67; H, 5.31; N, 9.99; Cl, 6.35.

Workup

  1. customthe solvent is removed under reduced pressure
  2. customthe residual solid is triturated with methanol

Sources & evidence

ORD record
ord-18b459ff237944839600a7e30b91789b
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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