Sodium Bicarbonate → HCID 86627645, compound

HRID 2167189Notes

Reaction equation

HRID 2167189 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].C([N:15]1[CH2:20][CH:19]=[C:18]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=2[NH:28][C:29](=[O:37])[C:30]2[CH:35]=[CH:34][N:33]=[C:32]([Cl:36])[CH:31]=2)[CH2:17][CH2:16]1)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Cl:7][CH:5]([O:4][C:2]([N:15]1[CH2:16][CH:17]=[C:18]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=2[NH:28][C:29]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([Cl:36])[CH:31]=2)=[O:37])[CH2:19][CH2:20]1)=[O:3])[CH3:6]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5213051-Chloroethyl chloroformateHCID 57577286HCID 57577286, compound

Product 1

HCID 86627645HCID 86627645, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Chloroethyl chloroformate (2.64 ml) was added to a suspension of N-[2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-chloro-phenyl]-2-chloro-isonicotinamide (530 mg) in toluene (30 ml). After 15 min. the solution was heated to reflux for 16 hours, then poured into saturated aqueous NaHCO3 solution and the mixture extracted three times with CH2Cl2. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford the crude title product (550 mg).

Workup

  1. temperatureAfter 15 min. the solution was heated
  2. temperatureto reflux for 16 hours
  3. extractionthe mixture extracted three times with CH2Cl2
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-448424ba01384e688e02f5d598005ebf
Source dataset
uspto-grants-2015_06
Patent number
US09045422B2

Reaction notes

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