Diisopropylethylamine → HCID 90011519, compound

HRID 1481485Notes

Reaction equation

HRID 1481485 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]3[NH:21][C:20](=[O:22])[O:19][N:18]=3)=[N:9]2)=[N:6][CH:7]=1.[CH3:23]CN(C(C)C)C(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([F:14])([F:16])[F:15])=[CH:11][C:10]([C:17]3[N:21]([CH3:23])[C:20](=[O:22])[O:19][N:18]=3)=[N:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 136501902HCID 136501902, compound

Product 1

HCID 90011519HCID 90011519, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Step-4: 3-(1-(5-Bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-3-yl)-1,2,4-oxadiazol-5(4H)-one: To a stirred and (0° C.) cooled solution of step-3 intermediate (106 mg, 0.303 mmol) and DIPEA (0.106 mL, 0.606 mmol) in DCM (15 mL) was added drop-wise a solution of triphosgene (35 mg, 0.121 mmol) in DCM (3 mL). The reaction was stirred at room temperature for 1 h before quenching with ice water (5 mL). Water (10 mL) was added to the above mixture followed by DCM (25 mL). The layers were separated and the aqueous layer was extracted with DCM (2×15 mL). The combined organic layers were washed with brine (15 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 100 mg (88%) of the title compound as brown solid. ESI-MS (m/z) 376, 378 [(MH)+, Br79,81].

Workup

  1. custombefore quenching with ice water (5 mL)
  2. additionWater (10 mL) was added to the above mixture
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (2×15 mL)
  5. washThe combined organic layers were washed with brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe filtrate was rotary evaporated

Sources & evidence

ORD record
ord-2b99415bd77b4acd8d8d71ca56e4fcd8
Source dataset
uspto-grants-2016_08
Patent number
US09409898B2

Reaction notes

Loading…