Dimethylformamide → {[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-thiophen-2-yl-acetic acid

HRID 1625475노트

반응식

HRID 1625475 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:5][N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([OH:14])=O)[C:7]1=[O:15].CN(C)C=O.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[NH2:58][CH:59]([C:63]1[S:64][CH:65]=[CH:66][CH:67]=1)[C:60]([OH:62])=[O:61]>>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:5][N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([NH:58][CH:59]([C:63]2[S:64][CH:65]=[CH:66][CH:67]=2)[C:60]([OH:62])=[O:61])=[O:14])[C:7]1=[O:15]

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 894352-Thiopheneacetic acid, alpha-amino-, (-)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534279691-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

생성물 1

HCID 68609732{[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-thiophen-2-yl-acetic acid

실험 절차

1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid (0.23 g, 0.00088 mol;) was dissolved in N,N-Dimethylformamide (9 mL, 0.1 mol;) and N,N-Diisopropylethylamine (800 uL, 0.004 mol;), and N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (0.37 g, 0.00097 mol;) were added. After 5 minutes preactivation Amino-thiophen-2-yl-acetic acid (0.266 g, 0.00169 mol;) was added. Workup consisted of rinsing with 5% citric acid then brine after dissolving the crude in ethyl acetate. The organic layer was then dried with magnesium sulfate and concentrated. The crude material was brought on directly to the next step. ES (+) MS m/e=404.81

후처리

  1. washof rinsing with 5% citric acid
  2. dissolutionbrine after dissolving the crude in ethyl acetate
  3. dry with materialThe organic layer was then dried with magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-77a74c3d608d4e909e1c6e502de692a2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778977B2

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