Ammonium Chloride → HCID 44540570, compound

HRID 402573Notes

Reaction equation

HRID 402573 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[C:4]2[O:12][C:13]([CH3:17])([CH3:16])[O:14][CH2:15][C:3]=12.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.[Cl-].[NH4+]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][C:2]2[CH:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[C:4]3[O:12][C:13]([CH3:17])([CH3:16])[O:14][CH2:15][C:3]=23)=[O:24])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 678794-Fluorobenzoyl chlorideHCID 44540569HCID 44540569, compound

Product 1

HCID 44540570HCID 44540570, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of methyl 5-amino-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate (23c) (70 mg, 0.25 mmol), 4-fluorobenzoyl chloride (35 μL, 0.27 mmol) and 4-dimethylaminopyridine in pyridine (1 mL) was stirred at room temperature overnight and a saturated solution of ammonium chloride was added. The reaction mixture was extracted with dichloromethane (3×25 mL) and the combined organic layers were dried (anh. Na2SO4), filtered and concentrated under reduced pressure to give methyl 5-(4-fluorobenzamido)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate (23d) as a white solid MS-ESI m/z 361 [MH]+.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (3×25 mL)
  2. dry with materialthe combined organic layers were dried (anh. Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b35c83868bc7470584c835cb07fea2d1
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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