Hydrochloric Acid → HCID 67465313, compound

HRID 1620003Notes

Reaction equation

HRID 1620003 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH2:10][NH:11][CH2:12][CH2:13][C:14]=3[N:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH:17][CH:18]([CH2:22][CH3:23])[C:19](O)=[O:20].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[OH:17][CH:18]([CH2:22][CH3:23])[C:19]([N:11]1[CH2:12][CH2:13][C:14]2[N:15]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][C:9]=2[CH2:10]1)=[O:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 112662-Hydroxybutyric AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 513585022-Phenyl-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine

Product 1

HCID 67465313HCID 67465313, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

1.14 g (4.80 mmol) 2-phenyl-4,5,6,7-tetrahydro-oxazolo[5,4-c]pyridine×HCl, 500.00 g (4.80 mmol) 2-hydroxybutanoic acid are placed in 10 mL DMF. Then 2.60 mL (18.51 mmol) triethylamine and 2.10 g (5.52 mmol) HATU are added and the mixture is stirred for 30 min at RT. The DMF is eliminated i.V., the residue is added to DCM and extracted 1 time each with 5% potassium hydrogen carbonate solution and 1N HCl. The solvent of the org. phase is eliminated in vacuo and the residue is purified on silica gel. (Eluant: cyclohexane/EA).

Workup

  1. extractionextracted 1 time each with 5% potassium hydrogen carbonate solution and 1N HCl
  2. customthe residue is purified on silica gel

Sources & evidence

ORD record
ord-49608400fb6241beb9fc6b63ea3a68af
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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