Formaldehyde → HCID 10230704, compound

HRID 1168526Notes

Reaction equation

HRID 1168526 reaction equation
[CH2:1]=O.[CH2:3]([NH:10][CH2:11][C:12]1[CH:13]=[C:14]([CH2:34][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][C:18]([C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)=[O:23])=[C:17]2[OH:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[CH2:11][C:12]2[C:21]3=[C:16]([C:17](=[O:33])[C:18]([C:22]([NH:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)=[O:23])=[CH:19][N:20]3[CH2:1]1)[CH:15]=[C:14]([CH2:34][N:35]1[CH2:36][CH2:37][O:38][CH2:39][CH2:40]1)[CH:13]=2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 178522895HCID 178522895, compound

Product 1

HCID 10230704HCID 10230704, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous formaldehyde (0.25 ml, 37% solution) is added to a solution of 8-((benzylamino)methyl)-N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (Preparation 29, 60 mg) in methanol (2.5 mL) at 50° C. The solution is allowed to cool and the resulting precipitate is filtered and washed with methanol to give 38 mg of the title compound. Physical characteristics: M.p. 203-205° C.; 1H NMR (DMSO-d6) δ2.38, 3.57, 3.73, 4.20, 4.57, 5.29, 7.2-7.4, 7.51, 8.08, 8.74, 10.4. Anal. Found: C, 68.50; H, 5.72; N, 10.29.

Workup

  1. temperatureto cool
  2. filtrationthe resulting precipitate is filtered
  3. washwashed with methanol

Sources & evidence

ORD record
ord-7a6b18497d084bcfba36116398e3515b
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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