Ammonium Chloride → HCID 178420398, compound

HRID 2306735Notes

Reaction equation

HRID 2306735 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]4[NH:30][N:29]=[N:28][N:27]=4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22609759(4-Benzyloxy-phenyl)-(6-cyanoquinazolin-4-yl)-amine

Product 1

HCID 178420398HCID 178420398, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

(4-Benzyloxy-phenyl)-(6-cyanoquinazolin-4-yl)-amine (0.106 g) in dimethylformamide was treated with sodium azide (0.06 g) and ammonium chloride (0.05 g) and the mixture stirred at 180° C. for 18 hours. The mixture was cooled, poured onto water and extracted with ethyl acetate/THF (3:1). The organic extracts were dried and concentrated in vacuo. The residue was purified using solid phase extraction to yield the title compound (0.024 g); δ H [2H6]DMSO 10.18(1H, s), 9.25(1H, s), 8.55(1H, s), 8.40(1H, d), 7.88(1H, d), 7.74(2H, d), 7.45(6H, m), 7.07(2H, d), 5.17(1H, s); m/z (M+1)+ 396.

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate/THF (3:1)
  4. customThe organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. extractionsolid phase extraction

Sources & evidence

ORD record
ord-4b580b2e51ae4b3395a1fa3b71a338ab
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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