Triethylamine → 3-[2-((R)-sec-Butylamino)-3,4-dioxo-cyclobut-1-enylamino]-6-chloro-N-ethyl-2-hydroxy-N-methoxy-benzenesulfonamide

HRID 516905

반응식

HRID 516905 반응식
[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:14][CH3:15])[CH2:12][CH3:13])(=[O:10])=[O:9])=[C:6]([OH:16])[C:5]([NH:17][C:18]2[C:21](=O)[C:20](=[O:23])[C:19]=2[O:24]CC)=[CH:4][CH:3]=1.[NH2:27][C@@H:28]([CH2:30][CH3:31])[CH3:29].C(N(CC)CC)C>CC#N.CCO>[C@H:28]([NH:27][C:21]1[C:20](=[O:23])[C:19](=[O:24])[C:18]=1[NH:17][C:5]1[C:6]([OH:16])=[C:7]([S:8]([N:11]([CH2:12][CH3:13])[O:14][CH3:15])(=[O:10])=[O:9])[C:2]([Cl:1])=[CH:3][CH:4]=1)([CH2:30][CH3:31])[CH3:29]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 2724537(R)-sec-butylamineHCID 866386316-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide

생성물 1

HCID 446291483-[2-((R)-sec-Butylamino)-3,4-dioxo-cyclobut-1-enylamino]-6-chloro-N-ethyl-2-hydroxy-N-methoxy-benzenesulfonamide

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

To a stirred solution of 6-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide (Intermediate FA) (100 mg, 0.25 mmol) in MeCN (1 ml) and EtOH (1 ml) was added (R)-(−)-2-Aminobutane (30.7 mg, 0.42 mmol) followed by triethylamine (69 μl, 0.49 mmol). The reaction mixture was heated at 70° C. for 1 hour. The reaction mixture was concentrated in vacuo and dissolved in EtOAc. The EtOAc solution was washed with 1M HCl (aq) and concentrated in vacuo. The residue was triturated with DCM to give a white solid; [M+H]+ 432.2. 1H NMR (DMSO) 0.9 (3H, t, CH3), 1.2 (6H, m), 1.5-1.6 (2H, m), 3.3 (2H, m), 3.7 (3H, s, CH3) 4.1 (1H, m), 7.3 (1H, d), 8.1 (1H, d), 8.3 (1H, d), 9.4 (1H, s), 10.1 (1H, s).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washThe EtOAc solution was washed with 1M HCl (aq)
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with DCM
  6. customto give a white solid

출처 및 근거

ORD 기록
ord-0dd69455878a41d58c7dbe10e0749291
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115087B2

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