Triethylamine → HCID 54764319, compound

HRID 244274Notes

Reaction equation

HRID 244274 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH:17]3[OH:22])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>C(Cl)Cl>[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][N:19]2[CH2:20][CH2:21][CH:16]([N:13]3[CH2:14][CH2:15][CH:10]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[O:9])[CH2:11][CH2:12]3)[CH:17]([OH:22])[CH2:18]2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 680214-Fluorobenzyl bromideHCID 67993102HCID 67993102, compound

Product 1

HCID 54764319HCID 54764319, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a solution of 13a (132 mg, 0.42 mmol) and triethylamine (17.1 mg, 1.69 mmol) in CH2Cl2 (15 mL), a solution of 4-fluorobenzyl bromide (80 mg, 0.42 mmol) in CH2Cl2(5 mL) was slowly added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with water (20 mL×2) and brine solution (20 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatograph using triethylamine/ethyl acetate (1/50, v/v) as mobile phase to afford free base 14a as pale yellow oil (78.9 mg, 45%). 1H NMR (CDCl3): δ 1.53-2.04 (m, 9H), 2.20-2.32 (m, 2H), 2.71-2.76 (m, 2H), 2.91-3.01 (m, 2H), 3.17-3.22 (m, 2H), 3.51-3.63 (m, 3H), 6.96-7.02 (m, 2H), 7.10-7.17 (m, 2H), 7.23-7.27 (m, 2H), 7.93-7.98 (m, 2H). Free base was converted to the oxalate salt by dissolving it in acetone and mixing with 1 equivalent of oxalic acid in acetone. mp: 234° C. (decomposed). Anal. (C24H28F2N2O2.H2C2O4.0.25H2O) C, H, N.

Workup

  1. washThe reaction mixture was washed with water (20 mL×2) and brine solution (20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by silica gel column chromatograph

Sources & evidence

ORD record
ord-a59f9b56895f4a52b3c3bab125bac655
Source dataset
uspto-grants-2014_02
Patent number
US08658131B2

Reaction notes

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