Ethyl Acetate → HCID 59596367, compound

HRID 2264573Notes

Reaction equation

HRID 2264573 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:13]2=3)=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH2:26][C:27]1[N:32]=[C:31](Cl)[CH:30]=[C:29]([Cl:34])[N:28]=1.[OH-].[Na+].CCOC(C)=O>CC(C)=O.O.CN(C=O)C>[F:25][C:2]([F:24])([F:1])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[C:20]([O:23][C:31]4[CH:30]=[C:29]([Cl:34])[N:28]=[C:27]([NH2:26])[N:32]=4)[CH:21]=[CH:22][C:13]2=3)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 86618286HCID 86618286, compound

Product 1

HCID 59596367HCID 59596367, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 567 mg (1.62 mMol) of 7-hydroxy-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide (Step 6.2), 532 mg (3.24 mMol) 2-amino-4,6-dichloro-pyrimidine and 145 mg (3.62 mMol) NaOH in 5 ml acetone, 7 ml H2O and 3 ml DMF is stirred at 60° C. for 24 h. Then it is poured into water and EtOAc, the aqueous phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/EtOAc 2:1→3:2) gives the title compound: m.p.: 175° C.; MS: [M+1]+=478/480; Anal.: C,H,N,Cl.

Workup

  1. customthe aqueous phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f08f0e704d144c2ab06f7ebdb90fbc2
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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