2-chloro-N-phenylquinazolin-4-amine → N-methyl-[4-(4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride

HRID 479281

Reaction equation

HRID 479281 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:19][NH:20][S:21]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)(=[O:23])=[O:22]>C(O)CC(C)C.C(O)C>[ClH:1].[CH3:19][NH:20][S:21]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:2]2[N:11]=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:27][CH:26]=1)(=[O:22])=[O:23]

Participants

5

Reactant 2

HCID 3179082-chloro-N-phenylquinazolin-4-amineHCID 27781314-Amino-N-methylbenzenemethanesulfonamide

Product 1

HCID 9825278N-methyl-[4-(4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31260Isoamyl AlcoholSolvent

Conditions

Temperature
170 °C

Procedure

A solution of 2-chloro-4-phenylamino-quinazoline (0.92 g) (prepared as described in Example 1a and N-methyl-(4-aminophenyl)-methanesulfonamide (0.80 g) in 10 ml of isopentylalcohol is stirred under nitrogen at 170° C. for 15 min in a sealed vessel. The warm reaction mixture is diluted with 10 ml ethanol and the hydrochloride salt, which is crystallizing on cooling, is filtered off to yield N-methyl-[4-(4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride as light yellow crystals melting at 259-263° C.; Rf (A2) 0.11, FAB-MS: (M+H)+=420. Analytical data: C22H21N5O2S+HCl.

Workup

  1. customThe warm reaction mixture
  2. customthe hydrochloride salt, which is crystallizing
  3. temperatureon cooling
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-55d099f9a42843b19cfeaa9173d2580b
Source dataset
uspto-grants-2003_11
Patent number
US06645774B1

Linked notes

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