Sodium Iodide → HCID 178443979, compound

HRID 486086

Reaction equation

HRID 486086 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[F:36])=[O:27]>CN(C)C=O.C(OCC)(=O)C>[F:36][C:30]1[CH:31]=[C:32]([F:35])[CH:33]=[CH:34][C:29]=1[NH:28][C:26](=[O:27])[N:25]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][S:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10342005N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylureaHCID 178527819HCID 178527819, compound

Product 1

HCID 178443979HCID 178443979, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Part B. A 100 mL flask was charged with 2-mercaptoimidazo[4,5-b]-pyridine (0.65 g, 0.0043 mol), sodium iodide (0.129 g, 0.00086 mol), and potassium carbonate (0.789 g, 0.00571 mol) in N,N-dimethylformamide (15 mL). A solution of N-(5-bromopentyl)-N-heptyl-N'-(2,4-difluorophenyl)urea (2.34 g, 0.00558 mol) in N,N-dimethylformamide (20 mL) was added and the mixture was heated to 60° C. under nitrogen atmosphere for 18 hours, then cooled and poured into ethyl acetate (100 mL). The ethyl acetate solution was washed with water (3×100 mL), dried over magnesium sulfate and concentrated. Purification by flash chromatography of the resulting residue afforded the product, which solidified upon standing overnight. The residue was recrystallized to afford the title compound (2.13 g, 0.0043 mol) as a viscous oil. 1H NMR (CDCl3) δ8.27 (dd,1H,J=5.2, 1.4 Hz), 8.06-7.98 (m,1H), 7.91 (dd,1H,J=7.9, 1.3 Hz), 7.18 (dd,1H,J=7.9, 4.9 Hz), 6.84-6.76 (m,1H), 6.49 (d,1H,J=3.3 Hz), 3.41-3.24 (m,6H), 1.94-1.84 (m,2H), 1.74-1.51 (m,6H), 1.35-1.23 (m,8H), 0.88 (t,3H,J=6.6 Hz).

Workup

  1. temperaturecooled
  2. washThe ethyl acetate solution was washed with water (3×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification by flash chromatography of the resulting residue
  6. customafforded the product, which
  7. customThe residue was recrystallized

Sources & evidence

ORD record
ord-7e27aa2317d24042b58255345e6a845c
Source dataset
uspto-grants-1994_03
Patent number
US05290801

Linked notes

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