2-(Dimethylamino)ethanol → 4-amino-2-butyl-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

HRID 1256075노트

반응식

HRID 1256075 반응식
Br[C:2]1[CH:3]=[C:4]([NH:22]C(=O)C(F)(F)F)[CH:5]=[CH:6][C:7]=1[S:8](=[O:21])(=[O:20])[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:17][O:16][B:15]([OH:18])[C:14]=2[CH:19]=1.[CH2:29]([Sn]([CH2:41][CH2:42][CH2:43][CH3:44])(CCCC)C#CC)[CH2:30][CH2:31]C.CN(CCO)C>CN1C(=O)CCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:22][C:4]1[CH:5]=[CH:6][C:7]([S:8]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[CH2:17][O:16][B:15]([OH:18])[C:14]=3[CH:19]=2)(=[O:21])=[O:20])=[C:2]([C:29]#[C:30][CH3:31])[CH:3]=1.[NH2:22][C:4]1[CH:5]=[CH:6][C:7]([S:8]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[CH2:17][O:16][B:15]([OH:18])[C:14]=3[CH:19]=2)(=[O:20])=[O:21])=[C:2]([CH2:41][CH2:42][CH2:43][CH3:44])[CH:3]=1

참가 물질

7

반응물 3

HCID 79022-(Dimethylamino)ethanolHCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 86655204N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide

생성물 2

HCID 671733494-amino-2-butyl-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamideHCID 67173444HCID 67173444, 화합물

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

The mix of compound N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide (87 mg, 0.182 mmol), tributyl(prop-1-ynyl)stannane (75.8 mg, 0.2 mmol), dimethylamino ethanol (17.9 mg, 0.2 mmol) and Pd(dppf)2Cl2 in NMP (2 ml) was degassed and heated to 100° C. overnight. The reaction mixture was washed with H2O, 1N NaOH and brine, dried over MgSO4, filtered and evaporated in reduced pressure to dryness. The residue was dissolved in 7N NH3/MeOH and stirred at 40° C. for 12 hrs. Evaporated to dryness and purified by prep-HPLC to give the desired compound 4-amino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(prop-1-ynyl)benzenesulfonamide and 4-amino-2-butyl-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide.

후처리

  1. customwas degassed
  2. washThe reaction mixture was washed with H2O, 1N NaOH and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in reduced pressure to dryness
  6. dissolutionThe residue was dissolved in 7N NH3/MeOH
  7. customEvaporated to dryness
  8. custompurified by prep-HPLC

출처 및 근거

ORD 기록
ord-c075ae0762aa470d8a3783b79d7f1e31
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461134B2

반응 노트

불러오는 중…