Triethylamine → HCID 11648256, compound

HRID 1864776Notes

Reaction equation

HRID 1864776 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[C:29]3[C:33](=[CH:34][CH:35]=2)[NH:32][CH:31]=[CH:30]3)=[CH:23][C:13]=1[CH2:14][NH:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:15]([CH2:14][C:13]2[CH:23]=[C:24]([C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[NH:32][CH:31]=[CH:30]4)[CH:25]=[CH:26][C:12]=2[F:11])[CH2:16][CH2:17][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 68746920HCID 68746920, compound

Product 1

HCID 11648256HCID 11648256, compoundYield 145.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorobenzoyl chloride (93 mg, 0.59 mmol) was added to a solution of [2-fluoro-5-(1H-indol-5-yl)-benzyl]-(2-pyrrolidin-1-yl-ethyl)-amine (90 mg, 0.27 mmol) and triethyl amine (81 mg, 0.8 mmol) in 10 ml of dichloromethane at room temperature. The resulting mixture was stirred at ambient temperature for 2 h, and then the volatiles were removed in vacuo and the residue was dissolved in ethyl acetate and washed with 1 M HCl solution and water. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with methanol/dichloromethane) provided 181 mg of product. This was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated to afford 92 mg of the title compound. LC/MS: Retention time, 2.55 min; (M+H)=460.

Workup

  1. customthe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 1 M HCl solution and water
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto leave the crude product
  9. washChromatography (elution with methanol/dichloromethane)

Sources & evidence

ORD record
ord-3ae86950e7444220b6c0c8927815127d
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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