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Acetic Acid → HCID 56847104, 화합물

HRID 1771843
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HRID 1771843 반응식
[CH2:1]([NH:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[N:17]=[C:16]([C:21](OC)=[O:22])[CH:15]=[CH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].[NH2:26][OH:27].C(O)(=O)C>CO>[CH2:1]([NH:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[N:17]=[C:16]([C:21]([NH:26][OH:27])=[O:22])[CH:15]=[CH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 66778751HCID 66778751, 화합물HCID 86662665HCID 86662665, 화합물

생성물 1

HCID 56847104HCID 56847104, 화합물수율 36%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a vial containing methyl 6-(benzylcarbamoyl)-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) and the resulting mixture was shaken at rt for 13 h. The solution was quenched with acetic acid (0.200 mL, 3.52 mmol) before being concentrated. To the resulting residue was added DMSO (1.2 mL) and it was purified via prep-HPLC to yield N6-benzyl-N2-hydroxy-7,8-dihydro-1,6-naphthyridine-2,6(5 H)-dicarboxamide (0.0113 g, 36.0%). LC-MS: (FA) ES+ 327; 1H NMR (Methanol-d4, 400 MHz) δ 7.86 (d, J=7.8 Hz, 1 H), 7.70 (d, J=8.0 Hz, 1 H), 7.25-7.19 (m, 5 H), 4.68 (s, 2 H), 4.39 (s, 2 H), 3.79 (t, J=6.0 Hz, 2 H), 3.03 (t, J=6.0 Hz, 2 H).

후처리

  1. concentrationbefore being concentrated
  2. additionTo the resulting residue was added DMSO (1.2 mL) and it
  3. customwas purified via prep-HPLC

출처 및 근거

ORD 기록
ord-f5c04c102be1455ba2e3a95ab98f80ba
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249142B2

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