Triethylamine → 7-(3-Methylaminosulfonylphenyl)-1-(4-methyl-1-piperazinyl)naphthalene

HRID 235131

반응식

HRID 235131 반응식
C[Sn](C)(C)[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.[CH3:22][NH:23][S:24]([C:27]1[CH:28]=[C:29](Br)[CH:30]=[CH:31][CH:32]=1)(=[O:26])=[O:25].C(N(CC)CC)C.[Cl-].[Li+]>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:22][NH:23][S:24]([C:27]1[CH:28]=[C:29]([C:3]2[CH:12]=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[C:10]3[N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)=[CH:5][CH:4]=2)[CH:30]=[CH:31][CH:32]=1)(=[O:25])=[O:26]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 433294Lithium Chloride2회HCID 72132653-bromo-N-methylbenzene-1-sulfonamideHCID 221156087-Trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene

생성물 1

HCID 189675037-(3-Methylaminosulfonylphenyl)-1-(4-methyl-1-piperazinyl)naphthalene

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

실험 절차

7-Trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene (0.25 g, 0.67 mmol), 3-methylaminosulfonyl-1-bromobenzene (0.18 g, 0.72 mmol), triethylamine (0.45 mL, 3.23 mmol), lithium chloride (0.088 g, 2.07 mmol), and bis (triphenylphosphine) palladium chloride (0.025 g, 0.036 mmol) were combined in DMF (12.5 mL) and heated to 110° to 110° C. for 45 minutes. The reaction was cooled to room temperature and 1 N aqueous lithium chloride (20 mL) was added. The mixture was extracted with ether (2x). The combined organic layer was washed with 1N lithium chloride and brine; then it was dried over magnesium sulfate and concentrated to an orange oil. Flash chromatography on silica gel (1×6 inches) with an ethyl acetate/hexane gradient of from 50 to 75% followed by continued elution with ethyl acetate and finally 5% methanol/ethyl acetate 0.11 g (42%) of the title product. The sample was recrystallized from ethyl acetate for analysis: mp 147.5°-148° C. Analysis calculated for C22H25N3O2S: C, 66.81; H, 6.31; N, 10.62. Found: C, 66.32; H, 6.16; N, 10.41.

후처리

  1. temperatureheated to 110° to 110° C. for 45 minutes
  2. extractionThe mixture was extracted with ether (2x)
  3. washThe combined organic layer was washed with 1N lithium chloride and brine
  4. dry with materialthen it was dried over magnesium sulfate
  5. concentrationconcentrated to an orange oil
  6. washFlash chromatography on silica gel (1×6 inches) with an ethyl acetate/hexane gradient of from 50 to 75% followed by continued elution with ethyl acetate and finally 5% methanol/ethyl acetate 0.11 g (42%) of the title product
  7. customThe sample was recrystallized from ethyl acetate for analysis

출처 및 근거

ORD 기록
ord-55ef8c79fecf408fa2af79218c67052f
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597826

연결된 노트

불러오는 중…