Dimethylamine → HCID 69839823, compound

HRID 2416248Notes

Reaction equation

HRID 2416248 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]([C@@H:13]1[CH2:15][C@H:14]1[C:16]([OH:18])=O)=[O:12].C(C1NC=CN=1)([C:21]1[NH:22][CH:23]=CN=1)=O.CNC>O1CCCC1>[CH3:21][N:22]([CH3:23])[C:16]([C@@H:14]1[CH2:15][C@H:13]1[C:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[NH:7][CH:6]=1)=[O:12])=[O:18]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 69841526HCID 69841526, compound

Product 1

HCID 69839823HCID 69839823, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trans-2-(5-fluoro-3-indolylcarbonyl)cyclopropanecarboxylic acid (1.5 g, 6 mmol) and carbonyl diimidazole in tetrahydrofuran was stirred for 0.5 hr. A solution of dimethylamine in tetrahydrofuran (3 ml, 2 M solution, 6 mmol) was added and the solution stirred for 3 hr. The solution was concentrated in vacuo and the residue dissolved in ethyl acetate. The organic solution was washed with 1 N HCl and saturated sodium bicarbonate solution. The solution was dried over sodium sulfate and concentrated in vacuo. The residue was triturated with isopropyl ether to give 1.5 g of trans-2-(5-fluoro-3-indolylcarbonyl)cyclopropanecarboxylic acid dimethylamide, mp 239-241° C. LC/MS mw=274; retention time 1.23 min. Mol wt calc1d for C15H15FN2O2: 274.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic solution was washed with 1 N HCl and saturated sodium bicarbonate solution
  4. dry with materialThe solution was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-03219594fccd4f1298c969426dee5e2e
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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