4-Chlorobenzylamine → HCID 9805202, compound

HRID 2119332Notes

Reaction equation

HRID 2119332 reaction equation
Br[CH2:2][C:3](OC(=O)CBr)=[O:4].ClC1C=CC(CN[C:17]([C:19]2[CH:20]=[N:21][C:22]3[C:27]([C:28]=2[OH:29])=[CH:26][C:25]([CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[CH:24][C:23]=3[NH:37][CH3:38])=[O:18])=CC=1.[Cl:41][C:42]1[CH:49]=[CH:48][C:45]([CH2:46][NH2:47])=[CH:44][CH:43]=1>C1COCC1.C(N(CC)CC)C.CO>[Cl:41][C:42]1[CH:49]=[CH:48][C:45]([CH2:46][NH:47][C:17]([C:19]2[C:28](=[O:29])[C:27]3[C:22]4[N:21]([CH:20]=2)[CH2:2][C:3](=[O:4])[N:37]([CH3:38])[C:23]=4[CH:24]=[C:25]([CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH:26]=3)=[O:18])=[CH:44][CH:43]=1

Participants

7

Reactant 3

HCID 660364-ChlorobenzylamineHCID 4259817Bromoacetic anhydrideHCID 178482192HCID 178482192, compound

Product 1

HCID 9805202HCID 9805202, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

A solution of bromoacetic anhydride (1.03 g, 4 mmol) in THF (3.0 mL) is added over 30 min to a stirred solution of N-(4-chlorobenzyl)-4-hydroxy-8-(methylamino)-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (308 mg of a 1:1 mixture of compound 9 and 4-chlorobenzylamine), triethylamine (500 mg, 5 mmol) in THF (7.0 mL). After 5 h, methanol (20 mL) and triethylamine (300 mg) are added, and the solution is stirred at room temperature overnight. The solution is evaporated, dissolved in chloroform/methanol, and is applied in chloroform to a silica gel column which is eluted with chloroform and then with 5-10% methanol/chloroform to give the title compound (98 mg) which is precipitated from acetonitrile.

Workup

  1. customThe solution is evaporated
  2. dissolutiondissolved in chloroform/methanol
  3. washis eluted with chloroform

Sources & evidence

ORD record
ord-772b9929fc0343f6a2d370a12caf8c8b
Source dataset
uspto-grants-2004_02
Patent number
US06686356B2

Reaction notes

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