Ammonium Chloride → HCID 86705052, compound

HRID 1427266Notes

Reaction equation

HRID 1427266 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([N:25]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([CH2:14][CH3:15])[C:9]#[C:10][C:11](O)=[O:12])=[CH:4][CH:3]=1.CC[N:40](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([N:25]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:36])[CH3:37])[S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([CH2:14][CH3:15])[C:9]#[C:10][C:11]([NH2:40])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86705051HCID 86705051, compound

Product 1

HCID 86705052HCID 86705052, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from step B (40 mg, 0.071 mmol, enantiomer A) in DMF (5 mL) was added DIPEA (18 mg, 0.142 mmol), HATU (40 mg, 0.11 mmol), NH4Cl (38 mg, 0.71 mmol). The mixture was stirred at RT overnight. After removing the organic solvent, the residue was dissolved with H2O (20 mL), extracted with ethyl acetate, and washed with brine, dried over sodium sulfate, then filtered. The solvent was evaporated and the residue was purified by Prep-TLC (EA/PE=2:1) to obtain the title compound. LC/MS m/z=582.0 [M+Na]+.

Workup

  1. customAfter removing the organic solvent
  2. dissolutionthe residue was dissolved with H2O (20 mL)
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customthe residue was purified by Prep-TLC (EA/PE=2:1)

Sources & evidence

ORD record
ord-ab268847b7bb40f297ba9d85f1b48fd4
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

Loading…