1-Butanol → HCID 24878128, compound

HRID 2091959Notes

Reaction equation

HRID 2091959 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:16]=[CH:15][C:11]([N:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[O:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1.C(O)CCC>CN(C=O)C.CO>[CH3:13][N:12]([CH3:14])[C:11]1[CH:15]=[CH:16][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:27][C:26]3[CH:25]=[CH:24][C:23]([N:20]4[CH2:21][CH2:22][O:17][CH2:18][CH2:19]4)=[CH:29][CH:28]=3)[N:7]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 534858024-(2-chloropyrimidin-4-yl)-N,N-dimethylaniline

Product 1

HCID 24878128HCID 24878128, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A flask was charged with C3 (500 mg, 2.1 mmol), 4-morpholinoaniline (573 mg, 3.2 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 67 was purified by HPLC with TFA/ACN as eluent. The TFA salt was removed by extracting with sodium hydroxide and ethylacetate to afford the free base of 67.

Workup

  1. customwas immersed in a 180° C.
  2. customfor 30 minutes
  3. customThe product 67 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-5c6a147afada45bea798e66cff076766
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

Loading…