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

HRID 1791722Notes

Reaction equation

HRID 1791722 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-01d532ea73d146a0826d5a2a83c5d8b3
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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