Sodium Iodide → HCID 59463660, compound

HRID 1713114Notes

Reaction equation

HRID 1713114 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:14]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9][C:8]=2[N:7]=[CH:6][N:5]=1.Cl[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([CH:25]2[CH2:28][CH2:27][CH2:26]2)[CH2:21][CH2:20]1)=[O:18].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C>[CH:25]1([N:22]2[CH2:23][CH2:24][N:19]([C:17](=[O:18])[CH2:16][N:11]3[CH2:12][CH2:13][C:14]4[C:4]([Cl:3])=[N:5][CH:6]=[N:7][C:8]=4[CH2:9][CH2:10]3)[CH2:20][CH2:21]2)[CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazineHCID 57420573HCID 57420573, compound

Product 1

HCID 59463660HCID 59463660, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine dihydrochloride (0.57 g, 2.2 mmol), 2-chloro-1-(4-cyclobutyl-piperazin-1-yl)-ethanone (0.48 g, 2.2 mmol), K2CO3 (1 g, 7.2 mmol), and NaI (0.33 g, 2.2 mmol) in acetonitrile is stirred overnight at rt. The solvent is evaporated and water is added. The mixture is extracted with DCM. The combined organic layers are dried (MgSO4) and solvent removed in vacuo to give the crude product, which is purified by PTLC (5% MeOH in DCM) to give the title compound.

Workup

  1. customThe solvent is evaporated
  2. additionwater is added
  3. extractionThe mixture is extracted with DCM
  4. dry with materialThe combined organic layers are dried (MgSO4) and solvent
  5. customremoved in vacuo
  6. customto give the crude product, which
  7. customis purified by PTLC (5% MeOH in DCM)

Sources & evidence

ORD record
ord-29e0e1e7c8f04fcf86a48eb176cc83cf
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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