Sodium Iodide → HCID 24751513, compound

HRID 1713108Notes

Reaction equation

HRID 1713108 reaction equation
[N:1]1[C:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]=2[CH:4]=[N:3][C:2]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1.Cl[CH:21]1[CH2:26][N:25]([CH:27]2[CH2:30][CH2:29][CH2:28]2)[CH2:24][CH2:23][NH:22]1.[C:31](N)(=[O:33])[CH3:32].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:2]2[N:3]=[CH:4][C:5]3[CH2:10][N:9]([CH2:32][C:31]([N:22]4[CH2:23][CH2:24][N:25]([CH:27]5[CH2:30][CH2:29][CH2:28]5)[CH2:26][CH2:21]4)=[O:33])[CH2:8][CH2:7][C:6]=3[N:1]=2)=[CH:12][CH:13]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 59463592HCID 59463592, compoundHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

Product 1

HCID 24751513HCID 24751513, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 1-[4-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-phenyl]-ethanone (253 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 (276 mg, 2.0 mmol, 2.0 eq.) and NaI (50 mg). The resulting mixture is stirred at 50° C. 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), and the combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by preparative silica gel flash chromatography (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.52 (2H, d), 8.48 (1H, s), 8.05 (2H, d), 3.78 (2H, s), 3.58˜3.72 (4H, m), 3.45 (2H, s), 3.09 (2H, t), 2.97 (2H, t), 2.69 (1H, m), 2.65 (3H, s), 2.29 (4H, m), 1.66˜2.08 (6H); MS (+VE) m/z 434.2 (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 preparative silica gel flash chromatography (EtOAc/4% TEA)

Sources & evidence

ORD record
ord-c6066d30e5f84281b859494172ae6761
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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