1,4-Dioxane hydrochloride → HCID 69345470, compound

HRID 1948231Notes

Reaction equation

HRID 1948231 reaction equation
Cl.O1CCOCC1.[Cl:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]2[C:19](=[O:20])[CH:18]=[CH:17][C:16]([C:21]3[CH:26]=[CH:25][C:24]([NH:27]C(=O)OC(C)(C)C)=[CH:23][CH:22]=3)=[CH:15]2)=[C:11]([F:37])[CH:10]=1>CO>[ClH:8].[Cl:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]2[CH:15]=[C:16]([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)[CH:17]=[CH:18][C:19]2=[O:20])=[C:11]([F:37])[CH:10]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69438746HCID 69438746, compound

Product 1

HCID 69345470HCID 69345470, compoundYield 178%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

According to Scheme 19 Step 2: HCl/dioxane (10 eq, 4M, 5.00 mL) was added to a solution of tert-butyl 4-(1-(4-chloro-2-fluorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)phenylcarbamate (1 eq, 2.00 mmol, 1.00 g) in MeOH (20 mL) at 0° C. The reaction was stirred for 2 days at 80° C., then the solvent was concentrated and Et2O was added. The solid was filtered and dried to yield 1-(4-chloro-2-fluorobenzyl)-5-(4-aminophenyl)pyridin-2(1H)-one hydrochloride (1.78 mmol, 0.76 g, 89%) as a beige solid.

Workup

  1. concentrationthe solvent was concentrated
  2. additionEt2O was added
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-7b1d691b03fc49698f90f4e551ffef72
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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