tert-Butanol → HCID 66623412, compound

HRID 415019Notes

Reaction equation

HRID 415019 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:32][CH3:33])=[C:25]([O:28]C(=O)C)[CH:26]=2)[N:21]=[CH:20][N:19]=1.CC(O)(C)C>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:32][CH3:33])=[C:25]([OH:28])[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 167812123-Chloro-4-(2-pyridylmethoxy)anilineHCID 220221604-Chloro-7-methoxyquinazolin-6-yl acetate

Product 1

HCID 66623412HCID 66623412, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamine (3.9 g, 16.62 mmol) and acetic acid 4-chloro-7-methoxy-quinazolin-6-yl ester (4.62 g, 18.28 mmol) were dissolved in a 1:1 mixture of DCE:t-BuOH (50 mL). The reaction mixture was refluxed for 19 hours and then cooled to room temp. Solvent was removed via rotovap. The crude residue was then suspended in MeOH (80 mL) and NH4OH (8 mL, 30% in water) was added to the mixture. Stir for 15 hours at room temp. The reaction was heated to 100° C. and stirred for 1 hour. Cool to 0° C. and product was isolated by filtration and washed with cold MeOH to give 5 g (12.2 mmol, 67% over two steps) of desired product.

Workup

  1. temperatureThe reaction mixture was refluxed for 19 hours
  2. customSolvent was removed via rotovap
  3. additionNH4OH (8 mL, 30% in water) was added to the mixture
  4. temperatureThe reaction was heated to 100° C.
  5. stirringstirred for 1 hour
  6. temperatureCool to 0° C.
  7. customproduct was isolated by filtration
  8. washwashed with cold MeOH

Sources & evidence

ORD record
ord-191611df4d16471cb9904eadc4fb60c0
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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