Diisopropylethylamine → HCID 24784536, compound

HRID 1993735Notes

Reaction equation

HRID 1993735 reaction equation
Cl[C:2](Cl)([O:4][C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([NH:25][C@H:26](C)[CH2:27]O)[S:23][CH:24]=2)=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:21]=[C:22]([N:25]3[C@H:26]([CH3:27])[CH2:2][O:4][C:5]3=[O:11])[S:23][CH:24]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 86618494HCID 86618494, compound

Product 1

HCID 24784536HCID 24784536, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphosgene (2.62 g, 8.82 mmol) in 60 mL of methylene chloride was added under nitrogen dropwise over 1.75 h to a solution of (2R)-2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}propan-1-ol (2.30 g, 7.33 mmol), prepared in the previous step, and N,N-diisopropylethylamine in 125 mL of methylene chloride at ice-bath temperature. After the addition the reaction was stirred at ice-bath temperature for 3.5 h. The ice bath was removed and the stirring continued for 15 h. The reaction was extracted with 2 N HCl, dried (anhydrous MgSO4), filtered and the solvent removed under reduced pressure to give 2.81 g of a yellow solid. Purification on the solid on 500 g of silica gel (230-400 mesh) using 30% methylene chloride-hexane to methylene chloride as the eluents gave the title compound (2.07 g, 83%) as a white solid, mp 197-199° C.; MS (ES) m/z 339.0 [M+H]+; Anal. Calcd for C13H11BrN2O2S: C, 46.03; H, 3.27; N, 8.26. Found: C, 45.80; H, 3.13; N, 8.16.

Workup

  1. additionAfter the addition the reaction
  2. customThe ice bath was removed
  3. waitthe stirring continued for 15 h
  4. extractionThe reaction was extracted with 2 N HCl
  5. dry with materialdried (anhydrous MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-67f35e20453b44d69fdcf1d5c1eb0d3f
Source dataset
uspto-grants-2010_01
Patent number
US07652018B2

Reaction notes

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