1-Hydroxybenzotriazole → HCID 86667063, compound

HRID 1626296Notes

Reaction equation

HRID 1626296 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C@H:10]([CH2:14][CH:15]=[CH2:16])[C:11]([OH:13])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH:17]1[CH:18]=[CH:19][C:20]2N(O)N=[N:23][C:21]=2[CH:22]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1[C:42]2N=CC=[CH:46][C:41]=2N=N1.CCN(C(C)C)C(C)C.C(N[C@@H]1CCCN([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])C1)C=C>CN(C=O)C>[CH2:46]([N:23]([C@@H:21]1[CH2:22][CH2:17][CH2:18][CH:19]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[CH2:20]1)[C:11](=[O:13])[C@H:10]([NH:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:14][CH:15]=[CH2:16])[CH:41]=[CH2:42]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67033348HCID 67033348, compoundHCID 67973728HCID 67973728, compound

Product 1

HCID 86667063HCID 86667063, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (R)-2-(3-chloro-5-fluoro-phenylamino)-pent-4-enoic acid (0.98 g, 4.1 mmol), HOBt (0.6209 g, 4.055 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (1.542 g, 4.055 mmol) and DIEA (1.8 mL, 10.1 mmol) in DMF (5 mL) was stirred for 5 minutes in an ice bath. Then (R)-tert-butyl 3-(allylamino)piperidine-1-carboxylate (0.97 g, 4.1 mmol) was added and the mixture stirred over night at rt. The mixture was poured into ice cold brine and extracted with EtOAc. The organic phase was separated, dried over (MgSO4), filtered and concentrated in vacuo to afford a residue which was purified by flash chromatography (silica 80 g, DCM/MeoH 0-5%) to afford 0.65 g, 34%. LCMS m/z 409.9 [M-tBu]+

Workup

  1. stirringthe mixture stirred over night at rt
  2. additionThe mixture was poured into ice cold brine
  3. extractionextracted with EtOAc
  4. customThe organic phase was separated
  5. dry with materialdried over (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a residue which
  9. customwas purified by flash chromatography (silica 80 g, DCM/MeoH 0-5%)
  10. customto afford 0.65 g, 34%

Sources & evidence

ORD record
ord-accb808345734229b22fd9b21530b689
Source dataset
uspto-grants-2014_07
Patent number
US08785440B2

Reaction notes

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