Hydrochloric Acid → HCID 178502725, compound

HRID 1631437Notes

Reaction equation

HRID 1631437 reaction equation
CN[O:3][CH3:4].Cl.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2N=N1.[CH2:33]([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])[CH3:34].[CH3:40][N:41]([CH:43]=[O:44])C>O>[CH2:33]([N:35]([CH2:38][C:39]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:16]=1)[C@H:36]1[CH2:21][CH2:20][C@H:19]([C:43]([N:41]([O:3][CH3:4])[CH3:40])=[O:44])[CH2:18][CH2:37]1)[C:34]1[CH:16]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 178502725HCID 178502725, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture of 13C (1 g, 3.09 mmol) in DMF (5 mL) was treated with N,O-dimethylhydroxylamine.HCl (0.452 g, 4.64 mmol), BOP (1.778 g, 4.02 mmol) and triethylamine (1.293 mL, 9.28 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with water and the resulting white solid was collected by filtration, and rinsed with water and air dried to provide 13D (1.2 g, >quantitative yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.29 (d, 4H, J=7.0 Hz); 7.17-7.26 (m, 4H); 7.10-7.16 (m, 2H); 3.61 (s, 3H); 3.56 (s, 4H); 3.08 (s, 3H); 2.44-2.59 (m, 2H); 1.85-1.95 (m, 2H); 1.70-1.82 (m, 2H); 1.28-1.45 (m, 4H).

Workup

  1. filtrationthe resulting white solid was collected by filtration
  2. washrinsed with water and air
  3. customdried

Sources & evidence

ORD record
ord-b8dfcfb168654f28a81d4888ccb0a346
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

Loading…