2-Propanol, reaction products with ammonia, distn. residues → 5-(3-chlorophenyl)-alpha-(4-chlorophenyl)-alpha-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine

HRID 347006노트

반응식

HRID 347006 반응식
[NH3:1].CC(O)C.Cl[C:7]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)([C:28]1[N:32]([CH3:33])[C:31]([S:34][CH3:35])=[N:30][N:29]=1)[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]1[N:18]=[N:19][N:20]=[C:13]1[N:12]=[C:11]2[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1>C1COCC1>[Cl:27][C:23]1[CH:22]=[C:21]([C:11]2[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([C:7]([C:36]4[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=4)([C:28]4[N:32]([CH3:33])[C:31]([S:34][CH3:35])=[N:30][N:29]=4)[NH2:1])[CH:9]=3)[N:14]3[N:18]=[N:19][N:20]=[C:13]3[N:12]=2)[CH:26]=[CH:25][CH:24]=1

참가 물질

4

반응물 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 210820857-[chloro(4-chlorophenyl)[4-methyl-5-(methylthio)-4H-1,2,4triazol-3-yl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a)quinazoline

생성물 1

HCID 210820625-(3-chlorophenyl)-alpha-(4-chlorophenyl)-alpha-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine수율 18%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

NH3/iPrOH saturated solution (40 ml) was added dropwise at 0° C. to a solution of 7-[chloro(4-chlorophenyl)[4-methyl-5-(methylthio)-4H-1,2,4triazol-3-yl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a)quinazoline (0.0036 mol) in THF (80 ml). The mixture was stirred from 0° C. to room temperature then at room temperature for 2 hours, poured out into ice water and extracted with EtOAc. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue (2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 98/2/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.35 g (18%) of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-α-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]-tetrazolo[1,5-a]quinazoline-7-methanamine. A sample (0.15 g) was crystallized from CH3CN/diethyl ether. The precipitate was filtered off and dried, yielding 0.05 g of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-α-[4methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]-tetrazolo[1,5-a]quinazoline-7-methanamine, mp. 150° C.

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 98/2/0.1; 15–40 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-728695abbde64105847111e3aa0210e3
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173040B2

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