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

HRID 2306756Notes

Reaction equation

HRID 2306756 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-1071ecf4057e41529cc849b4bf3edab7
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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