Sodium Iodide → HCID 178506037, compound

HRID 1672466Notes

Reaction equation

HRID 1672466 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[C:15]([NH:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([NH2:25])[CH2:21][CH2:20]2)[N:14]=[CH:13]3)[CH2:3][CH2:2]1.Br[CH2:27][CH2:28][F:29].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[F:29][CH2:28][CH2:27][NH:25][C@H:22]1[CH2:23][CH2:24][C@H:19]([NH:18][C:15]2[N:14]=[CH:13][C:12]3[C:17](=[C:8]([O:7][CH:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[CH:9]=[CH:10][CH:11]=3)[N:16]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 178511656HCID 178511656, compound

Product 1

HCID 178506037HCID 178506037, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trans-N-[8-(tetrahydro-2H-pyran-4-yloxy)quinazolin-2-yl]cyclohexane-1,4-diamine (0.4 g, 1.168 mmol) and 1-bromo-2-fluoro-ethane (0.178 g, 1.4 mmol) in anhydrous DMF (10 mL) were added anhydrous K2CO3 (0.4035 g, 2.92 mmol) and NaI (0.0174 g, 0.1168). The resulting mixture was stirred at room temperature for 72 h. The mixture was concentrated and CH2Cl2 (40 mL) was added to the residue. The mixture was washed with H2O (3×30 mL) and brine (30 mL), dried over Na2SO4 and concentrated in vacuo to give crude solid, which was purified by chromatography (CH2Cl2: MeOH=40:1) to give the title compound (0.150 g, 33.3%) as a yellow solid. 1H NMR (CDCl3, 400 Hz): 8.872 (s, 1H), 7.273 (d, 1H), 7.130 (d, 1H), 7.038 (t, 1H), 5.129 (s, 1H), 4.568 (s, 1H), 4.556 (t, 1H), 4.449 (t, 1H), 3.995 (m, 2H), 3.897 (m, 1H), 3.493 (m, 2H), 2.925 (t, 1H), 2.854 (t, 1H), 2.491 (m, 1H), 2.201 (s, 2H), 1.970 (m, 6H), 1.214 (m, 5H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionCH2Cl2 (40 mL) was added to the residue
  3. washThe mixture was washed with H2O (3×30 mL) and brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give crude solid, which
  7. customwas purified by chromatography (CH2Cl2: MeOH=40:1)

Sources & evidence

ORD record
ord-c89140c692c048978eb6ffb86aa90c62
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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