Ammonia → 5-(2-Chloro-4-morpholino-quinazolin-7-yl)furan-2-carbonitrile

HRID 517470

Reaction equation

HRID 517470 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([C:18]3[O:22][C:21]([CH:23]=O)=[CH:20][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1.II.[NH3:27]>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([C:18]3[O:22][C:21]([C:23]#[N:27])=[CH:20][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 807IodineHCID 866657705-(2-Chloro-4-morpholino-quinazolin-7-yl)furan-2-carbaldehyde

Product 1

HCID 866657725-(2-Chloro-4-morpholino-quinazolin-7-yl)furan-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a 50 mL round bottom flask, 5-(2-chloro-4-morpholino-quinazolin-7-yl)furan-2-carbaldehyde (0.48 g, 0.0014 mol; prepared in a similar method to that described in Example 10) and THF (10 mL) were added. To the same flask, iodine (0.39 g, 0.00154 mol) and 30% aqueous ammonia (9.6 mL) were added. The reaction mixture was stirred at 25° C. The light brown reaction mixture turned yellow after 3 h. The reaction was quenched by adding ethyl acetate (100 mL) and 10% aqueous sodium thiosulfate (40 mL) and stirred for 5 min. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure to get the crude product. The crude product was purified using column chromatography (60-120 silica gel, 10-50% ethyl acetate in hexane) to yield the desired product as an off white solid [0.31 g, 65%]. 1H NMR (300 MHz, CDCl3): δ 8.11 (s, 1H), 7.92 (d, J=9.0 Hz, 1H), 7.78 (d, J=9.0 Hz, 1H), 7.24 (d, J=3.6 Hz, 1H), 6.95 (d, J=3.6 Hz, 1H), 3.95 (s, 8H). LC-MS (ESI): Calculated mass: 340.0; Observed mass: 341.0 (RT: 1.55 min).

Workup

  1. customprepared in a similar method to
  2. additionwere added
  3. customThe reaction was quenched
  4. additionby adding ethyl acetate (100 mL) and 10% aqueous sodium thiosulfate (40 mL)
  5. stirringstirred for 5 min
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure
  10. customto get the crude product
  11. customThe crude product was purified

Sources & evidence

ORD record
ord-4db595b00e39455aa29a58ea430bbd42
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Linked notes

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