Triethylamine → HCID 86708260, compound

HRID 534212Notes

Reaction equation

HRID 534212 reaction equation
[CH:1]([O-:3])=[O:2].[K+].C(N(CC)CC)C.[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][N:26]([C@@H:33]2[CH2:35][C@H:34]2[C:36]2[CH:41]=[CH:40][C:39](I)=[CH:38][CH:37]=2)[C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Li+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:12]([N:19]1[CH2:20][CH2:21][CH:22]([CH2:25][N:26]([C@@H:33]2[CH2:35][C@H:34]2[C:36]2[CH:37]=[CH:38][C:39]([C:1]([OH:3])=[O:2])=[CH:40][CH:41]=2)[C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH2:23][CH2:24]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 433294Lithium ChlorideHCID 2735122Potassium FormateHCID 86708258HCID 86708258, compound

Product 1

HCID 86708260HCID 86708260, compoundYield 12.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a 10-mL of microwave tube were added potassium formate (88 mg, 1.051 mmol), triethylamine (0.098 mL, 0.701 mmol) acetic anhydride (0.066 mL, 0.701 mmol) and DMF (1 mL), the resulting solution was stirred at room temperature for 1 h. N-((1-benzylpiperidin-4-yl)methyl)-2,2,2-trifluoro-N-((trans)-2-(4-iodophenyl)cyclopropyl)acetamide (190 mg, 0.350 mmol), Pd2(dba)3 (8.02 mg, 8.76 mmol), and lithium chloride (44.6 mg, 1.051 mmol) in DMF (1 mL) were added. The tube was sealed and the mixture was stirred at 80° C. for 4 h. The mixture was concentrated and the residue was taken up in methanol and filtered. The filtrate was purified using reverse-phase HPLC to give 20 mg of product as off-white solid. MS: (M+H)+=461.3. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.40-1.62 (m, 3H), 1.65-1.78 (m, 1H), 1.87-2.01 (m, 2H), 2.07 (d, J=13.39 Hz, 1H), 2.51-2.62 (m, 1H), 2.80-3.00 (m, 2H), 3.20-3.71 (m, 6H), 4.23 (s, 2H), 7.21 (d, J=8.34 Hz, 2H), 7.42-7.54 (m, 5H), 7.95 (d, J=8.34 Hz, 2H).

Workup

  1. customThe tube was sealed
  2. stirringthe mixture was stirred at 80° C. for 4 h
  3. concentrationThe mixture was concentrated
  4. filtrationfiltered
  5. customThe filtrate was purified

Sources & evidence

ORD record
ord-3a5e1977c00b438183f540976556cb36
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

Loading…