1-Butanol → HCID 24877326, compound

HRID 2091958Notes

Reaction equation

HRID 2091958 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[O:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.C(O)CCC>CN(C=O)C.CO>[N:21]1([C:24]2[CH:25]=[CH:26][C:27]([NH:28][C:2]3[N:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=4)[CH:5]=[CH:4][N:3]=3)=[CH:29][CH:30]=2)[CH2:20][CH2:19][O:18][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 44754979HCID 44754979, compound

Product 1

HCID 24877326HCID 24877326, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A flask was charged with C1 (500 mg, 2.0 mmol), 4-morpholinoaniline H (540 mg, 3.0 mmol) and nBuOH (10 mL). The flask was immersed in a 180° C. oil bath for 30 minutes. The reaction mixture was cooled to ambient temperature and the black residue dissolved in DMF and MeOH. The product was purified by HPLC with TFA/ACN as eluent. The TFA salt was removed by extracting with sodium hydroxide and ethylacetate to afford the title compound (18).

Workup

  1. customwas immersed in a 180° C.
  2. customfor 30 minutes
  3. customThe product was purified by HPLC with TFA/ACN as eluent
  4. customThe TFA salt was removed
  5. extractionby extracting with sodium hydroxide and ethylacetate

Sources & evidence

ORD record
ord-aa5608b8d9cf4b32bbe31d3f640dc3f8
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

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