Pyridine → HCID 178517747, compound

HRID 968615Notes

Reaction equation

HRID 968615 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].N1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C[O:28][CH2:29][CH2:30][CH2:31][C:32](Cl)=O.[OH-].[Na+].[CH2:37]1COC[CH2:38]1>>[CH2:22]([O:28][CH2:29][CH2:30][CH2:31][C:32]1[N:6]=[C:4]([OH:5])[C:3]2[C:2](=[CH:10][C:9]([C:11]3[C:16]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:8][CH:7]=2)[N:1]=1)[C:23]1[CH:38]=[CH:37][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 5

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 127949894-Methoxybutanoyl chlorideHCID 220300742-Amino4-(3-trifluoromethyl-pyridin-2-yl)-benzamide

Product 1

HCID 178517747HCID 178517747, compound

Procedure

To a solution of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide (3.56 mmol) and pyridine (3.91 mmol) in THF (20 ml), add 4-methoxy-butyryl chloride (3.91 mmol). Stir the mixture 20 minutes at room temperature, add 20 ml of 20% NaOH, stir for 60 minutes at 50° C. Concentrate, add water, filter, acidify to pH=6, collect the precipitate to obtain 2-(3-benzyloxy-propyl)7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-ol.

Workup

  1. stirringstir for 60 minutes at 50° C
  2. concentrationConcentrate
  3. additionadd water
  4. filtrationfilter
  5. customcollect the precipitate

Sources & evidence

ORD record
ord-1b6a5f2766a648ea91d09bec347c192f
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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