Sodium Iodide → HCID 24751653, compound

HRID 1713129Notes

Reaction equation

HRID 1713129 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[CH:12]1[CH2:17][N:16]([CH:18]2[CH2:21][CH2:20][CH2:19]2)[CH2:15][CH2:14][NH:13]1.[C:22](N)(=[O:24])[CH3:23].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[CH:18]1([N:16]2[CH2:15][CH2:14][N:13]([C:22](=[O:24])[CH2:23][N:7]3[CH2:8][CH2:9][C:10]4[N:1]=[CH:2][CH:3]=[CH:4][C:5]=4[CH2:6]3)[CH2:12][CH2:17]2)[CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 131938825,6,7,8-Tetrahydro-1,6-naphthyridineHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

Product 1

HCID 24751653HCID 24751653, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 5,6,7,8-tetrahydro-[1,6]naphthyridine (134 mg, 1.0 mmol) in acetonitrile (5.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (216 mg, 1.0 mmol, 1.0 eq.), K2CO3 (376 mg, 2.0 mmol, 2.0 eq.), and NaI (30 mg). The resulting mixture is stirred at rt overnight. Water (10.0 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3). The combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by PTLC (EtOAc/4% TEA/4% EtOH) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.40 (1H, dd), 7.30 (1H, dd), 7.06 (1H, dd), 3.70 (2H, s), 3.63 (4H, m), 3.38 (2H, s), 3.04 (2H, t), 2.89 (2H, t), 2.67 (1H, m), 2.27 (4H, m), 1.60-2.06 (6H, m); MS (+VE) m/z 315.2 (M++1).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile is evaporated
  4. extractionThe residue is extracted with DCM (10 ml×3)
  5. dry with materialThe combined organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by PTLC (EtOAc/4% TEA/4% EtOH)

Sources & evidence

ORD record
ord-525575c5ffe44424b8062bbf4033b7f1
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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