Diisopropylethylamine → HCID 88020671, compound

HRID 2306622Notes

Reaction equation

HRID 2306622 reaction equation
C(N(CC)C(C)C)(C)C.[CH:10]([C:12]1[CH:22]=[CH:21][C:15]([CH:16]=[CH:17][C:18]([OH:20])=O)=[CH:14][CH:13]=1)=[O:11].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:47][CH2:48][C@@H:49]1[O:53][C:52](=[O:54])[N:51]([C:55]2[CH:60]=[CH:59][C:58]([C:61]3[S:62][CH2:63][C:64](=[O:67])[NH:65][N:66]=3)=[C:57]([F:68])[CH:56]=2)[CH2:50]1>CN(C=O)C>[F:68][C:57]1[CH:56]=[C:55]([N:51]2[CH2:50][C@H:49]([CH2:48][NH:47][C:18](=[O:20])[CH:17]=[CH:16][C:15]3[CH:14]=[CH:13][C:12]([CH:10]=[O:11])=[CH:22][CH:21]=3)[O:53][C:52]2=[O:54])[CH:60]=[CH:59][C:58]=1[C:61]1[S:62][CH2:63][C:64](=[O:67])[NH:65][N:66]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23528997HCID 23528997, compound

Product 1

HCID 88020671HCID 88020671, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (0.169 ml, 0.972 mmol) is added to 4-formylcinnamic acid (0.057 g, 0.324 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.129 g, 0.340 mmol) in DMF (2 ml) and is stirred for 20 minutes at room temperature. 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-4H-[1,3,4]thiadiazin-5-one (0.100 g, 0.308 mmol) is added and stirring is continued at room temperature overnight. The reaction mixture is partially evaporated under vacuum and the residue is diluted with water (5 ml). The resulting precipitate is filtered and dried under vacuum to give crude product used directly in the next step (0.076 g, 51%). MS (m/z): [M+H]+=483.

Workup

  1. stirringstirring
  2. waitis continued at room temperature overnight
  3. customThe reaction mixture is partially evaporated under vacuum
  4. additionthe residue is diluted with water (5 ml)
  5. filtrationThe resulting precipitate is filtered
  6. customdried under vacuum
  7. customto give crude product

Sources & evidence

ORD record
ord-2ca73f563d81402984cf217da28cea94
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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