4-Amino-N-methylbenzenemethanesulfonamide → N-methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide

HRID 1739641

반응식

HRID 1739641 반응식
Cl[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]=[C:7]([O:19][CH3:20])[CH:8]=2)[N:3]=1.[CH3:21][NH:22][S:23]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1)(=[O:25])=[O:24]>C(O)CC(C)C.CO>[CH3:21][NH:22][S:23]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][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]=[C:7]([O:19][CH3:20])[CH:8]=3)[N:3]=2)=[CH:29][CH:28]=1)(=[O:24])=[O:25]

참가 물질

5

반응물 2

HCID 27781314-Amino-N-methylbenzenemethanesulfonamideHCID 226398172-Chloro-6-methoxy-4-phenylamino-quinazoline

생성물 1

HCID 22639807N-methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide

시약·촉매·용매 2

HCID 887Methanol용매HCID 31260Isoamyl Alcohol용매

실험 절차

A solution of 2-chloro-6-methoxy-4-phenylamino-quinazoline (1.15 g) and N-methyl-(4-aminophenyl)-methanesulfonamide (prepared as described in Tetrahedron Letters 1992, 33, 8011) (0.89 g) in 5 ml of isopentylalcohol is stirred under nitrogen at 180° C. for 20 min in a sealed vessel. The warm reaction mixture is diluted with methanol and the hydrochloride salt, which is crystallizing on cooling, is filtered off. The crude product is redissolved in ethylacetate and aqueous sodium carbonate solution and extracted with ethylacetate. The organic extracts are dried and evaporated and the solid residue is titurated with diethylether to give N-methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide as light yellow crystals melting at 212-215° C.; (Rf (A2) 0.16. Recrystallisation from methanolic hydrogen chloride and diethylether yields N-methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride as light yellow crystals melting at 264-268° C.; Rf (A2) 0.16, FAB-MS: (M+H)+ =450. Analytical data: C23H23N5O3S+HCl.

후처리

  1. customThe warm reaction mixture
  2. customthe hydrochloride salt, which is crystallizing
  3. temperatureon cooling
  4. filtrationis filtered off
  5. dissolutionThe crude product is redissolved in ethylacetate
  6. extractionaqueous sodium carbonate solution and extracted with ethylacetate
  7. customThe organic extracts are dried
  8. customevaporated

출처 및 근거

ORD 기록
ord-f432a98ad4a048b6a7e00b13853cd54a
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968819

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