Sodium Iodide → 2-[2-(4-Cyclobutyl-piperazin-1-yl)-2-oxo-ethyl]-1,2,3,4-tetrahydro-isoquinoline-7-carboxylic acid methylamide

HRID 1713092Notes

Reaction equation

HRID 1713092 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].Cl[CH:16]1[CH2:21][N:20]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[CH2:19][CH2:18][NH:17]1.[C:26](N)(=[O:28])[CH3:27].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C.O>[CH3:1][NH:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]([CH2:27][C:26]([N:17]3[CH2:18][CH2:19][N:20]([CH:22]4[CH2:25][CH2:24][CH2:23]4)[CH2:21][CH2:16]3)=[O:28])[CH2:12]2)=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 57479413N-methyl-1,2,3,4-tetrahydroisoquinoline-7-carboxamideHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

Product 1

HCID 594635382-[2-(4-Cyclobutyl-piperazin-1-yl)-2-oxo-ethyl]-1,2,3,4-tetrahydro-isoquinoline-7-carboxylic acid methylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1,2,3,4-tetrahydro-isoquinoline-7-carboxylic acid methylamide (96 mg, 0.5 mmol) in acetonitrile (3.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (109 mg, 0.5 mmol, 1.0 eq.), K2CO3 (138 mg, 1.0 mmol, 2.0 eq.), and NaI (10 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), and the combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by PTLC (EtOAc/4% TEA plus 4% EtOH) to give the title compound. MS (+VE) m/z 371.1 (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 plus 4% EtOH)

Sources & evidence

ORD record
ord-6f2e90cbc2974026a0b23207e1508234
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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