HCID 21101726, compound → HCID 21101723, compound

HRID 1353429Notes

Reaction equation

HRID 1353429 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][C:23](=[O:28])[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:29][Mg+].[Br-]>C1COCC1>[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][C:23]([OH:28])([CH3:29])[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21101726HCID 21101726, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 21101723HCID 21101723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(7-chloro-4-quinolinyl)-N-(3-oxocycloheptyl)-1-piperazinecarboxamide (8 mg, 0.02 mmol) in THF (3 mL) was added a solution of MeMgBr (3M, 0.1 mL) at 0° C. After 5 h at 0° C., the reaction mixture was quenched with MeOH and Na2CO3 (sat. 50 mL). The reaction mixture was extracted with CH2Cl2, washed with brine, and dried over Na2SO4. Concentration in vacuo followed by preparative TLC gave the title product. LC-MS: 401 (M++1). 1H NMR (CDCl3) δ 8.78 (d, 1H), 8.05 (s, 1H), 7.95 (d, 1H), 7.45 (m, 1H), 6.85 (d, 1H), 5.75 (d, 1H), 4.45 (d, 1H), 4.05 (m, 1H), 3.65 (m, 4H), 3.20 (m, 4H), 1.55–1.95 (m, 10H), 1.35 (s, 3H).

Workup

  1. customthe reaction mixture was quenched with MeOH and Na2CO3 (sat. 50 mL)
  2. extractionThe reaction mixture was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c012c654fef240dfbd29979e283c9e29
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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