Triethylamine → HCID 11597201, compound

HRID 1373619Notes

Reaction equation

HRID 1373619 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([NH2:30])=[N:5][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[CH:7][CH:8]=1.Cl[C:32](OC1C=CC=CC=1)=[O:33].CCN(CC)CC.[Li+].CC([N-]C(C)C)C>C1COCC1>[C:20]1([N:17]2[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][CH2:11][CH2:10][O:9][C:6]3[CH:7]=[CH:8][C:3]4[CH2:2][NH:1][C:32](=[O:33])[NH:30][C:4]=4[N:5]=3)[CH2:19][CH2:18]2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 2724682Lithium diisopropylamideHCID 21073299HCID 21073299, compound

Product 1

HCID 11597201HCID 11597201, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-aminomethyl-6-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-pyridin-2-ylamine (0.92 g, 2.27 mmol) in THF (25 mL) was treated with phenyl chloroformate (0.40 mL, 3.18 mmol) followed by Et3N (0.46 g, 4.54 mmol). The mixture was stirred at room temperature for 1 hour, then cooled to 0° C. and treated with LDA (5.6 mL, 11.20 mmol, 2.0 M in heptane/THF/ethylbenzene). The brown mixture was stirred at room temperature for 1 hour, then quenched with water and extracted with EtOAc. The organic extracts were washed with water, and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (2.5% Et3N/EtOAc) to afford the title compound as a light yellow solid (0.204 g, 21%). mp 136–138; 1H NMR (400 MHz, CDCl3): δ 8.24–8.16 (m, 1H), 7.85–7.78 (m, 1H), 7.55 (d, 1H), 7.50–7.42 (m, 2H), 7.40 (t, 1H), 7.25 (d, 1H), 7.09 (d, 1H), 6.84 (br s, 1H), 6.34 (d, 1H), 5.05 (br s, 1H), 4.48 (s, 2H), 4.45 (t, 2H), 3.30–2.05 (m, 4H), 2.93–2.60 (m, 4H), 2.55 (t, 2H), 1.90–1.70 (m, 4H). MS ES: m/z=432.11.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe brown mixture was stirred at room temperature for 1 hour
  3. customquenched with water
  4. extractionextracted with EtOAc
  5. washThe organic extracts were washed with water, and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (2.5% Et3N/EtOAc)

Sources & evidence

ORD record
ord-2195dfe4e1804e17b39595b1cd3256f3
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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