Triethylamine → HCID 3666186, compound

HRID 1050951Notes

Reaction equation

HRID 1050951 reaction equation
Br[C:2]1[C:15]2=[N:16][O:17][C:13]3=[C:14]2[C:5]([C:6](=[O:18])[C:7]2[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:4]([NH:19][C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)[CH:3]=1.C(N(CC)CC)C.[CH:36]1([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.CC(OC)(C)C>CS(C)=O.CO>[CH:36]1([N:42]2[CH2:47][CH2:46][N:45]([C:2]3[C:15]4=[N:16][O:17][C:13]5=[C:14]4[C:5]([C:6](=[O:18])[C:7]4[C:12]5=[CH:11][CH:10]=[CH:9][CH:8]=4)=[C:4]([NH:19][C:20]4[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=4)[CH:3]=3)[CH2:44][CH2:43]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 872981-CyclohexylpiperazineHCID 90410908HCID 90410908, compound

Product 1

HCID 3666186HCID 3666186, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Dissolving 4-((3-bromo-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzoic acid in DMSO, then adding triethylamine and 1-cyclohexyl piperazine (2a) into the solution. Raising temperature to 60-70° C. After 2-3 hours, slowly adding MTBE and MeOH solution and cooling to room temperature. Isolation and washing of the wet cake with MTBE and MeOH followed by filtering provided 4-((3-(4-cyclohexylpiperazin-1-yl)-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzoic acid (Intermediate 6) as a solid.

Workup

  1. washIsolation and washing of the wet cake with MTBE and MeOH
  2. filtrationby filtering

Sources & evidence

ORD record
ord-c1a66ba624e849b7b49f75f18a74dd85
Source dataset
uspto-grants-2016_07
Patent number
US09388146B2

Reaction notes

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