Hydrochloric Acid → 7-Benzyloxy-4(indol-5-ylamino)-6-methoxyquinazoline hydrochloride

HRID 454197Notes

Reaction equation

HRID 454197 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:19])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[CH:26]2.Cl>C(O)(C)C>[ClH:19].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[NH:28][CH:27]=[CH:26]4)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 788675-AminoindoleHCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline

Product 1

HCID 220305477-Benzyloxy-4(indol-5-ylamino)-6-methoxyquinazoline hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 7-benzyloxy-4-chloro-6-methoxyquinazoline (5 g, 16.6 mmol), (prepared as described for the starting material in Example 1), 5-aminoindole (2.4 g, 18.2 mmol) in isopropanol (60 ml) containing 5N hydrogen chloride in isopropanol (260 μl, 1.6 mmol) was refluxed for 90 minutes. After cooling the volatiles were removed under vacuum. The solid was triturated with isopropanol, filtered, washed with isopropanol followed by ether and dried under vacuum to give 7-benzyloxy-4-(indol-5-ylamino)-6-methoxyquinazoline hydrochloride (6.9 g, 96%).

Workup

  1. temperaturewas refluxed for 90 minutes
  2. temperatureAfter cooling the volatiles
  3. customwere removed under vacuum
  4. customThe solid was triturated with isopropanol
  5. filtrationfiltered
  6. washwashed with isopropanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0dcd299550ad4a7cbfd7e8b2cf6dcec5
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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