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Acetic Acid → HCID 56847160, 화합물

HRID 1847622
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HRID 1847622 반응식
[CH2:1]([S:5]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([C:18]([O:20]C)=O)[CH:12]=[CH:11][C:10]=2[CH2:9]1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[K].[NH2:23][OH:24].C(O)(=O)C>CO>[CH2:1]([S:5]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([C:18]([NH:23][OH:24])=[O:20])[CH:12]=[CH:11][C:10]=2[CH2:9]1)(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 66778571HCID 66778571, 화합물HCID 86662665HCID 86662665, 화합물

생성물 1

HCID 56847160HCID 56847160, 화합물수율 28.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a microwave vial containing methyl 6-(butylsulfonyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylate was added MeOH (1 mL) and hydroxylamine potassium salt (1 mL, 1.76 mmol, 1.76 M in MeOH). The solution was shaken at rt for 1 h, then acetic acid (0.102 mL, 1.8 mmol) was added to quench excess base. The solvent was then concentrated. To the resulting residue was added DMSO (1.2 mL) and after filtration, the solution underwent purification via prep-HPLC to give 6-(butylsulfonyl)-N-hydroxy-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxamide (13.3 mg, 28.3%). LC-MS: (FA) ES+ 314; 1H NMR (Methanol-d4, 300 MHz) δ 7.97 (d, J=8.1 Hz, 1 H), 7.76 (d, J=7.9 Hz, 1 H), 4.59 (s, 2 H), 3.70 (t, J=6.0 Hz, 2 H), 3.13 (m, 4 H), 1.77 (m, 2 H), 1.47 (m, 2 H), 0.95 (t, J=7.3 Hz, 3 H).

후처리

  1. customto quench excess base
  2. concentrationThe solvent was then concentrated
  3. additionTo the resulting residue was added DMSO (1.2 mL)
  4. filtrationafter filtration
  5. customthe solution underwent purification via prep-HPLC

출처 및 근거

ORD 기록
ord-594cbc7d6e6c43a989dcaebf349eca3a
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952163B2

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