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

HRID 1625475Notes

Reaction equation

HRID 1625475 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-77a74c3d608d4e909e1c6e502de692a2
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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