Triethylamine → HCID 22288504, compound

HRID 968221Notes

Reaction equation

HRID 968221 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[N:19]=[C:18]([S:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:17]=[C:16]([NH2:28])[C:15]=1[NH2:29].C(N(CC)CC)C>C(Cl)Cl>[Cl:13][C:14]1[N:19]=[C:18]([S:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:17]=[C:16]2[C:15]=1[NH:29][C:2](=[O:4])[NH:28]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 22288509HCID 22288509, compound

Product 1

HCID 22288504HCID 22288504, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of triphosgene (0.92 g) in DCM (25 ml) was added dropwise to a solution of the product from example 2, step (e) (0.69 g) and triethylamine (0.55 ml) in DCM (25 ml) at −10° C. The cooling bath was then removed and the suspension stirred for 2.5 h. Upon cooling to 0° C. NaHCO3 (20 ml) was added with vigorous stirring before recovering the organics by extracting with DCM (3×50 ml). The organic extracts were combined, dried (MgSO4) and concentrated in vacuo to yield a crude yellow solid. This material was triturated with EtOAc and filtered to afford a pink solid (360 mg, 48%). The filtrate was concentrated and again triturated with EtOAc to provide a second crop (170 mg, 70% overall)

Workup

  1. customThe cooling bath was then removed
  2. additionNaHCO3 (20 ml) was added
  3. stirringwith vigorous stirring
  4. custombefore recovering the organics
  5. extractionby extracting with DCM (3×50 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto yield a crude yellow solid
  9. customThis material was triturated with EtOAc
  10. filtrationfiltered

Sources & evidence

ORD record
ord-70ea319c75224517bfc9c44accc78698
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

Loading…