Hydrochloric Acid → HCID 16718426, compound

HRID 910410Notes

Reaction equation

HRID 910410 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[N:3]1[CH:16]([CH:20]([CH3:22])[CH3:21])[C:17](O)=[O:18].F[P-](F)(F)(F)(F)F.[N:30]1([O:39][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.ON.Cl.CN1CCOCC1>CN(C=O)C>[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[N:3]1[CH:16]([CH:20]([CH3:22])[CH3:21])[C:17]([NH:30][OH:39])=[O:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 76578026HCID 76578026, compound

Product 1

HCID 16718426HCID 16718426, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in step e above (109 mg, 0.36 mmol) in DMF (1.8 mL) was added BOP (190 mg, 0.43 mmol) at 0° C. After stirring for 30 min, HONH2×HCl (50 mg, 11.38 mmol) and N-methylmorpholine (0.16 mL, 1.44 mmol) were added. The mixture was warmed to room temperature and stirred overnight. The solvent was removed and the residue was partitioned between EtOAc and a saturated solution of NH4Cl. The aqueous layer was extracted with EtOAc, dried and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a white solid (63 mg, 55% yield).

Workup

  1. stirringstirred overnight
  2. customThe solvent was removed
  3. customthe residue was partitioned between EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-73d948267f6b4769abeb22820307445a
Source dataset
uspto-grants-2011_09
Patent number
US08022092B2

Reaction notes

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