Hydrochloric Acid → 2-(4-(4-Benzyloxy-phenylamino)-quinazolin-6-yl)-3-methyl-3H-imidazole-4-carbaldehyde

HRID 1936826Notes

Reaction equation

HRID 1936826 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]4[N:30]([CH3:31])[C:29]([CH:32]5OCC[O:33]5)=[CH:28][N:27]=4)[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.Cl>CC(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[N:30]([CH3:31])[C:29]([CH:32]=[O:33])=[CH: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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22609737(4-Benzyloxy-phenyl)-(6-(4-(1,3-dioxolan-2-yl)-3-methyl-3H-imidazol-2-yl)-quinazolin-4-yl)-amine

Product 1

HCID 226098202-(4-(4-Benzyloxy-phenylamino)-quinazolin-6-yl)-3-methyl-3H-imidazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(4-Benzyloxy-phenyl)-(6-(4-(1,3-dioxolan-2-yl)-3-methyl-3H-imidazol-2-yl)-quinazolin-4-yl)-amine (0.06 g) was treated with acetone (5 ml) and 2N HCl at reflux for 2 hours. The mixture was cooled, partitioned between ethyl acetate and 2N sodium carbonate. The organic phase was dried and concentrated in vacuo to give the title compound which was used directly in any subsequent synthetic step; m/z (M+1)+ 436.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture was cooled
  3. custompartitioned between ethyl acetate and 2N sodium carbonate
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8ce7fb30ca74862998ab064a225fb4c
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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