Methanol → HCID 3010832, compound

HRID 1168495Notes

Reaction equation

HRID 1168495 reaction equation
Br[CH2:2][C:3](OC(=O)CBr)=[O:4].[NH2:10][C:11]1[CH:12]=[C:13]([CH2:33][N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][C:17]([C:21]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)=[O:22])=[C:16]2[OH:32].C(N(CC)CC)C.CO>CN(C=O)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][NH:23][C:21]([C:17]2[C:16](=[O:32])[C:15]3[C:20]4[N:19]([CH:18]=2)[CH2:2][C:3](=[O:4])[NH:10][C:11]=4[CH:12]=[C:13]([CH2:33][N:34]2[CH2:35][CH2:36][O:37][CH2:38][CH2:39]2)[CH:14]=3)=[O:22])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471Triethylamine2×HCID 4259817Bromoacetic anhydride2×HCID 178507700HCID 178507700, compound

Product 1

HCID 3010832HCID 3010832, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Bromoacetic anhydride (290 mg) is added to a stirred solution of 8-amino-N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (Preparation 3, 426 mg) in anhydrous DMF (5.0 mL). After 30 min, triethylamine (100 mg) and additional bromoacetic anhydride (100 mg) are added. After 1 h, triethylamine (300 mg) is added and the solution is heated briefly at 80° C. Methanol (8 mL) is added and the resulting precipitate is filtered off, washed with water and dried to afford 262 mg of the title compound as a DMF solvate. Physical characteristics: 1H NMR (DMSO-d6) δ2.37, 2.73, 2.89, 3.53, 3.57, 4.56, 5.11, 7.23, 7.35, 7.40, 7.72, 7.95, 8.72, 10.35, 11.2.

Workup

  1. waitAfter 1 h
  2. filtrationthe resulting precipitate is filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-aec3249ff9d7437abf4958a8db5254f6
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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