Triethylamine → HCID 86708260, compound

HRID 529360Notes

Reaction equation

HRID 529360 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 μmol), 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-51e5beec828b4a0d9fc5fcac14f53ce1
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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