Dimethylformamide → HCID 66936976, compound

HRID 240589Notes

Reaction equation

HRID 240589 reaction equation
Cl.[N:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([OH:29])[CH:27]=5)[N:22]=[CH:21][N:20]=4)=[CH:14][C:13]=3[CH3:30])=[CH:7][C:6]=12.[CH:31]12[O:36][CH:35]1[CH2:34][CH2:33][CH2:32]2.O.[OH-].[Cs+].CN(C=O)C>O>[N:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([O:29][C@@H:34]6[CH2:33][CH2:32][CH2:31][C@H:35]6[OH:36])[CH:27]=5)[N:22]=[CH:21][N:20]=4)=[CH:14][C:13]=3[CH3:30])=[CH:7][C:6]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 23679066Caesium hydroxide--water (1/1/1)HCID 66937033HCID 66937033, compound

Product 1

HCID 66936976HCID 66936976, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
92 °C

Procedure

A 50 mL flask was charged with 4-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenylamino)quinazolin-6-ol hydrochloride (3.117 g, 7.406 mmol), 6-oxa-bicyclo[3.1.0]hexane (0.6924 ml, 7.777 mmol), cesium hydroxide monohydrate (2.736 g, 16.29 mmol), DMF (20 mL). The reaction was heated to 92° C. for 12 hours, then cooled to room temperature and dilute with 200 mL of water. The mixture was stirred for 24 hours. The resulting precipitate was collected by filtration, washed with water and air dried to provide 2.80 g of the title compound as a racemic mixture. MS APCI (+) m/z 469.3 (M+1) detected.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-2319ae8cb53040af8a8d5b7944ce5b7e
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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