Methyl iodide → HCID 21101725, compound

HRID 1353430Notes

Reaction equation

HRID 1353430 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([OH:28])[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31]I>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([O:28][CH3:31])[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21101724HCID 21101724, compound

Product 1

HCID 21101725HCID 21101725, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(7-chloro-4-quinolinyl)-N-(3-hydroxycycloheptyl)-1-piperazinecarboxamide (30 mg, 0.074 mmol) in DMF (3 mL) was added NaH (8.9 gm, 0.37 mmol) at rt. After 30 min, MeI (11.5 mg, 0.09 mmol) was added, and the reaction mixture was heated at rt for 2 h. After cooling to rt, the reaction mixture was quenched with MeOH, then poured into water (100 mL). The reaction mixture was extracted with EtOAc, washed with brine, and dried over Na2SO4. Concentration in vacuo followed by flash chromatography afforded the title product. LC-MS: 416 (M++1). 1H NMR (CDCl3) δ 8.75 (d, 1H), 8.05 (s, 1H), 7.95 (d, 1H), 7.45 (d, 1H), 6.85 (d, 1H), 4.40 (d, 1H), 4.10 (m, 1H), 3.65 (m, 4H), 3.45 (m, 1H), 3.36 (s, 3H), 3.20 (m, 4H), 2.15 (m, 1H) 2.05 (m, 1H), 1.50–1.90 (m, 6H), 1.40 (m, 2H).

Workup

  1. temperatureAfter cooling to rt
  2. customthe reaction mixture was quenched with MeOH
  3. additionpoured into water (100 mL)
  4. extractionThe reaction mixture was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-2cf7474610b147d7abc22a78c8a7f250
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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