Hydrochloric Acid → HCID 52933152, compound

HRID 536071Notes

Reaction equation

HRID 536071 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:11]([NH:14][CH3:15])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N:8]([CH3:10])[CH3:9].Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1.Cl>C(O)(C)C>[CH3:28][O:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][C:23]=1[O:29][CH3:30])[N:20]=[CH:19][N:18]=[C:17]2[NH:1][C:2]1[CH:3]=[C:4]([S:11]([NH:14][CH3:15])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N:8]([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 43449104HCID 43449104, compound

Product 1

HCID 52933152HCID 52933152, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 3-amino-4-(dimethylamino)-N-methylbenzenesulfonamide (0.100 g, 0.434 mmol) and 4-chloro-6,7-bis(methyloxy)quinazoline (0.075 g, 0.334 mmol) in isopropanol (2 mL) was added HCl (0.334 mL, 0.334 mmol). The resulting mixture was then subjected to microwave irradiation (150° C., 6 bar) for 15 minutes. The mixture was then concentrated and purified via column chromatography (5-10% MeOH/CH2Cl2) to give an orange solid that was triturated with EtOAc and dried to afford 3-{[6,7-bis(methyloxy)-4-quinazolinyl]amino}-4-(dimethylamino)-N-methylbenzenesulfonamide (54 mg, 35% yield) as orange crystals.

Workup

  1. customThe resulting mixture was then subjected to microwave irradiation (150° C., 6 bar) for 15 minutes
  2. concentrationThe mixture was then concentrated
  3. custompurified via column chromatography (5-10% MeOH/CH2Cl2)
  4. customto give an orange solid
  5. customthat was triturated with EtOAc
  6. customdried

Sources & evidence

ORD record
ord-9a9e0c07a099441cb025a1792f224414
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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