Triethylamine → HCID 73442067, compound

HRID 530690Notes

Reaction equation

HRID 530690 reaction equation
[N:1]([C:4]1[S:5][C:6]([CH3:19])=[C:7]([CH3:18])[C:8]=1[C:9]1[O:13][N:12]=[C:11]([C:14]([F:17])([F:16])[F:15])[N:10]=1)=[C:2]=[O:3].[NH:20]1[CH2:27][CH2:26][CH2:25][C@@H:21]1[C:22]([OH:24])=[O:23].C(N(CC)CC)C>C(Cl)Cl>[CH3:18][C:7]1[C:8]([C:9]2[O:13][N:12]=[C:11]([C:14]([F:17])([F:16])[F:15])[N:10]=2)=[C:4]([NH:1][C:2]([N:20]2[CH2:27][CH2:26][CH2:25][C@@H:21]2[C:22]([OH:24])=[O:23])=[O:3])[S:5][C:6]=1[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8988D-ProlineHCID 90046253HCID 90046253, compound

Product 1

HCID 73442067HCID 73442067, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 5-(2-isocyanato-4,5-dimethyl-thiophen-3-yl)-3-trifluoromethyl-[1,2,4]-oxadiazole (178 mg, 0.615 mmol) in CH2Cl2 (10 mL) were added D-proline (142 mg, 1.23 mmol) and triethylamine (0.128 mL, 0.923 mmol) at 25° C. and the reaction mixture was stirred at 25° C. for 12 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and washed with 2N aqueous HCl solution (15 mL) followed by H2O (20 mL). The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified using silica gel column chromatography using a gradient of CH2Cl2:MeOH (100:0 to 95:5) to furnish the desired compound as an off-white solid (120 mg, 48%). MS (ESI): m/z=403.4 (M−H)−.

Workup

  1. washwashed with 2N aqueous HCl solution (15 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-54a5e763b36546fd81194a6fcaca5eda
Source dataset
uspto-grants-2016_05
Patent number
US09353102B2

Reaction notes

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