1,1'-Carbonyldiimidazole → tert-Butyl (S)-1-(5-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

HRID 2075339Notes

Reaction equation

HRID 2075339 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([N:14]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:15][C@@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[N:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].C1N=CN([C:48](N2C=NC=C2)=[O:49])C=1>C1COCC1>[O:49]=[C:48]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3[S:13][C:12]([N:14]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:15][C@@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:17][C:18]4[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=4)=[N:11][N:10]=3)=[CH:3][C:2]=2[O:1]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57991851tert-Butyl (S)-1-(5-(3-hydroxy-4-aminophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Product 1

HCID 57991881tert-Butyl (S)-1-(5-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamateYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

tert-Butyl (S)-1-(5-(3-hydroxy-4-aminophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (200 mg, 328 μmol) was dissolved in 50 mL THF in a round bottom flask. To this flask was added CDI (213 mg, 1312 μmol). The mixture was stirred at 70° C. for 16 hours. After removing the solvent under reduced pressure, the remaining residue was mixed with 100 mL EtOAc. The organic solution was washed with water, saturated ammonium chloride twice and dried over sodium sulfate. After removing the solvent, the desired product (140 mg, 67%) was obtained as a tan solid. LCMS (API-ES) m/z (%): 636.0 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 1.23 (s, 9H) 1.58 (s, 9H) 2.82-2.96 (m, 1H) 2.95-3.08 (m, 1H) 4.12-4.27 (m, 1H) 4.32-4.43 (m, 2H) 7.15-7.25 (m, 1H) 7.49 (d, J=8.02 Hz, 2H) 7.60 (d, J=7.83 Hz, 2H) 7.70 (dd, J=8.12, 1.47 Hz, 1H) 7.76 (s, 1H).

Workup

  1. customAfter removing the solvent under reduced pressure
  2. additionthe remaining residue was mixed with 100 mL EtOAc
  3. washThe organic solution was washed with water, saturated ammonium chloride twice
  4. dry with materialdried over sodium sulfate
  5. customAfter removing the solvent

Sources & evidence

ORD record
ord-c20b72349d1545eab052ffd017711d2a
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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