Diisopropylethylamine → HCID 54710692, compound

HRID 2217211Notes

Reaction equation

HRID 2217211 reaction equation
[OH:1][C:2]1[C:3]2[CH:18]=[CH:17][S:16][C:4]=2[N:5]([CH:13]([CH3:15])[CH3:14])[C:6](=[O:12])[C:7]=1[C:8]([O:10]C)=O.[CH2:19]([N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)[CH3:20].C(N(C(C)C)CC)(C)C>C1(C)C(C)=CC=CC=1>[CH2:19]([N:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:8]([C:7]2[C:6](=[O:12])[N:5]([CH:13]([CH3:15])[CH3:14])[C:4]3[S:16][CH:17]=[CH:18][C:3]=3[C:2]=2[OH:1])=[O:10])[CH2:23][CH2:22]1)[CH3:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 37349901-Ethylpiperidin-4-amineHCID 54685950HCID 54685950, compound

Product 1

HCID 54710692HCID 54710692, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of methyl 6,7-dihydro-4-hydroxy-7-isopropyl-6-oxothieno-[2,3-b]pyridine-5-carboxylate (0.22 g, 0.82 mmol), 1-ethylpiperidin-4-amine (0.44 g, 1.24 mmol) and diisopropylethylamine (0.35 mL, 2.48 mmol) in xylene (3 mL) was heated at 120° C. for 2 h. The reaction mixture was cooled to room temperature, washed with water and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography eluted with 3% methanol-dichloromethane to give the title compound (0.20 g, 67% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 10.34 (br s, 1 H, 7.37 (d, 1 H, 6.95 (d, 1 H, 4.01 (m, 2 H, 3.03 (m, 2 H, 2.63 (d, 2 H, 2.41 (m, 2 H, 2.12 (d, 2 H, 1.81 (q, 2 H, 1.62 (d, 6 H, 1.18 (t, 3 H; MS: m/e 364 (M+H+).

Workup

  1. washwashed with water
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel flash column chromatography
  4. washeluted with 3% methanol-dichloromethane

Sources & evidence

ORD record
ord-e84c3dd021574259a1f12c8c08e71b78
Source dataset
uspto-grants-2008_08
Patent number
US07407966B2

Reaction notes

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