Sodium Iodide → HCID 58346558, compound

HRID 222016Notes

Reaction equation

HRID 222016 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]3[C:15]4[C:16]([O:20][CH2:21][CH2:22][C:23]5[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=5)=[N:17][CH:18]=[N:19][C:14]=4[S:13][C:10]=32)=[N:5]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH3:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>C(#N)C>[CH3:40][N:41]1[CH2:46][CH2:45][N:44]([CH2:2][CH2:3][N:4]2[CH:12]=[C:11]3[C:6]([CH2:7][CH2:8][C:9]4[C:15]5[C:16]([O:20][CH2:21][CH2:22][C:23]6[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=6)=[N:17][CH:18]=[N:19][C:14]=5[S:13][C:10]=43)=[N:5]2)[CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 58346735HCID 58346735, compound

Product 1

HCID 58346558HCID 58346558, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-(2-bromoethyl)-6-[2-(4-nitrophenyl)ethoxy]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazole (4.0 g, 7.99 mmol), K2CO3 (2.21 g, 15.99 mmol), and NaI (1.20 g, 7.99 mmol) in acetonitrile (300 mL) was added N-methyl piperazine (3.20 g, 31.98 mmol). Resulting mixture was heated at 80° C. for 4.5 h after which time analytical HPLC showed no more starting material present and a new major peak appeared. Solvents were evaporated and the residue was dissolved in water and CH2Cl2. The organic layer was separated, dried (Na2SO4), and concentrated to afford a light yellow solid. The solid material was further washed with ether, air-dried to afford a pale solid (4.14 g, 95%) as the desired product. 1H-NMR (DMSO-d6) δ 8.52 (s, 1H), 8.19 (d, 2H), 7.95 (s, 1H), 7.63 (d, 2H), 4.78 (t, 2H), 4.14 (t, 2H), 3.28 (t, 2H), 3.01 (t, 2H), 2.78 (t, 2H), 2.67 (t, 2H), 2.40 (broad, 4H), 2.26 (broad, 4H), 2.11 (s, 3H); LCMS RT=2.42 min; [M+H]+=520.2.

Workup

  1. customResulting mixture
  2. customSolvents were evaporated
  3. dissolutionthe residue was dissolved in water
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto afford a light yellow solid
  8. washThe solid material was further washed with ether
  9. customair-dried

Sources & evidence

ORD record
ord-adb213b80a924ff1a9f03e2959521600
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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