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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Hydroxyamine hydrochloride → N-[4-[(1R,3R,4Z,5S)-3-amino-4-hydroxyimino-5-methylcyclohexyl]-3-pyridinyl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide

HRID 705286
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인쇄 미리보기

반응식

HRID 705286 반응식
Cl.[NH2:2][OH:3].[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1[C:12]1[N:17]=[C:16]([C:18]([NH:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][C:26]=2[C@H:27]2[CH2:32][C@@H:31]([NH:33]C(=O)OC(C)(C)C)[C:30](=O)[C@@H:29]([CH3:42])[CH2:28]2)=[O:19])[CH:15]=[CH:14][C:13]=1[F:43]>CCO.N1C=CC=CC=1>[NH2:33][C@@H:31]1[CH2:32][C@H:27]([C:26]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[NH:20][C:18](=[O:19])[C:16]2[CH:15]=[CH:14][C:13]([F:43])=[C:12]([C:6]3[C:5]([F:4])=[CH:10][CH:9]=[CH:8][C:7]=3[F:11])[N:17]=2)[CH2:28][C@H:29]([CH3:42])/[C:30]/1=[N:2]/[OH:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 86705245tert-butyl (1R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-3-methyl-2-oxocyclohexylcarbamate

생성물 1

HCID 72548916N-[4-[(1R,3R,4Z,5S)-3-amino-4-hydroxyimino-5-methylcyclohexyl]-3-pyridinyl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide수율 14%

시약·촉매·용매 1

HCID 21975839Pyridine ethanol용매

실험 절차

A solution of hydroxylamine-HCl (4.0 equiv.) and tert-butyl (1R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-3-methyl-2-oxocyclohexylcarbamate (1.0 equiv.) in EtOH/pyridine (1/1, 0.01 M) was capped and left standing at rt for 16 hrs. The volatiles were removed in vacuo and the residue was partitioned between EtOAc and Na2CO3(sat.). The organic layer was washed with NaCl(sat), dried over MgSO4, filtered, concentrated. The Boc group was removed with 25% TFA/CH2Cl2. After 45 minutes, the volatiles were removed in vacuo and after pumping the residue was dissolved in DMSO and purified by RP-HPLC to yield N-(4-((1R,3R,5 S,Z)-3-amino-4-(hydroxyimino)-5-methylcyclohexyl)pyridin-3-yl)-6-(2,6-difluorophenyl)-5-fluoropicolinamide in 14% yield. LC/MS (m/z)=470.3 (MH+), Rt=0.60 min. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.94 (s, 1H), 10.49 (s, 1H), 8.60 (s, 1H), 8.48 (d, J=4.0, 1H), 8.35 (dd, J=8.0, 4.0, 1H), 8.20 (t, J=8.0, 1 H), 8.02 (broad doublet, J=4.0, 2H), 7.67-7.74 (m, 1H), 7.42 (d, J=4.0, 1H), 7.36 (t, J=8.0, 2H), 4.24 (m, 1H), 3.82-3.86 (m, 1H), 3.21-3.27 (m, 1H), 2.50-2.55 (m, 1H), 2.24 (d, J=12.0, 1H), 1.86 (d, J=16.0, 1H), 1.68 (q, J=12.0, 1H), 1.59 (q, J=12.0, 1H), 1.40 (d, J=8.0, 3H).

후처리

  1. waitleft
  2. customThe volatiles were removed in vacuo
  3. customthe residue was partitioned between EtOAc and Na2CO3(sat.)
  4. washThe organic layer was washed with NaCl(sat)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe Boc group was removed with 25% TFA/CH2Cl2
  9. waitAfter 45 minutes
  10. customthe volatiles were removed in vacuo
  11. dissolutionwas dissolved in DMSO
  12. custompurified by RP-HPLC

출처 및 근거

ORD 기록
ord-97855a5ea5a748b3b0d90696715a5004
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09173883B2

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