Sodium hydride → HCID 68679539, compound

HRID 1172434Notes

Reaction equation

HRID 1172434 reaction equation
[OH:1][NH:2][C:3](=[NH:5])[CH3:4].[H-].[Na+].[Cl:8][C:9]1[C:10]([F:43])=[C:11]([CH:40]=[CH:41][CH:42]=1)[C:12]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:22]=[C:23]([CH:28]=[C:29]([N:31]=[C:32]3[N:36]([CH2:37][O:38][CH3:39])[CH:35]=[CH:34][S:33]3)[N:30]=2)[C:24](OC)=O)[CH2:16][CH2:15]1)=[O:13]>O1CCCC1.C(OCC)(=O)C>[Cl:8][C:9]1[C:10]([F:43])=[C:11]([CH:40]=[CH:41][CH:42]=1)[C:12]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[N:30]=[C:29]([N:31]=[C:32]3[N:36]([CH2:37][O:38][CH3:39])[CH:35]=[CH:34][S:33]3)[CH:28]=[C:23]([C:24]3[O:1][N:2]=[C:3]([CH3:4])[N:5]=3)[CH:22]=2)[CH2:16][CH2:15]1)=[O:13]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 68677297HCID 68677297, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 68679539HCID 68679539, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 9.4 mg of N-hydroxyacetamidine, molecular sieves 4A and 1 ml of tetrahydrofuran was added sodium hydride followed by stirring at 65° C. for 1 hour. To the reaction solution was added a solution of 22.6 mg of methyl 2-((4-(3-chloro-2-fluorobenzoyl)piperazin-1-yl)methyl)6-((3-(methoxymethyl)-thiazol-2(3H)-ylidene)amino)isonicotinate in 1 ml of tetrahydrofuran, followed by heating under reflux for 6 hours. The reaction solution was cooled to room temperature, diluted with ethyl acetate, and washed with saturated sodium bicarbonate and brine. The resulting organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated. The resulting residue was purified by a thin-layer chromatography for fractionation (eluent: chloroform/methanol=10/1) to give the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. temperatureThe reaction solution was cooled to room temperature
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialThe resulting organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe resulting residue was purified by a thin-layer chromatography for fractionation (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-acaf3e3ce59f4071a7c91cbe04daef6a
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

Loading…