NRC-2694 → HCID 66924527, compound

HRID 1408473Notes

Reaction equation

HRID 1408473 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:30][CH3:31])=[C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]>C(OCC)(=O)C>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:30][CH3:31])=[C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

3

Reactant 1

HCID 16129168NRC-2694

Product 1

HCID 66924527HCID 66924527, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
67.5 °C

Procedure

Into a three liter three necked round bottomed flask equipped with a mechanical stirrer, reflux-condenser and thermometer socket were charged ethyl acetate (2000 ml), followed by N-(3-ethynylphenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-4-quinazolinamine (25 g) obtained from the process described in the above given Example-(1). The reaction mass was slowly heated to 65-70° C., so that the solid material completely dissolved and carbon treatment was given and filtered the reaction mass. The filtrate was transferred into another round-bottomed flask and slowly cooled to 10-15° C. and maintained for 30 minutes at that temperature. The crystalline mass was filtered and after washing the cake with chilled ethyl acetate dried to get 20.95 g of N-(3-ethylphenyl)-6-(3-morpholino propoxy)-7-methoxy-4-quinazolinamine as a white crystalline solid.

Workup

  1. customobtained from the process
  2. dissolutioncompletely dissolved
  3. filtrationfiltered the reaction mass
  4. customThe filtrate was transferred into another round-bottomed flask
  5. temperatureslowly cooled to 10-15° C.
  6. temperaturemaintained for 30 minutes at that temperature
  7. filtrationThe crystalline mass was filtered
  8. washafter washing the cake with chilled ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-92f5e9ff8ddc4d3eaf2117c3e92c9202
Source dataset
uspto-grants-2014_12
Patent number
US08921362B2

Reaction notes

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