Methyl bromoacetate → HCID 67272256, compound

HRID 1592594Notes

Reaction equation

HRID 1592594 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.Br[CH2:34][C:35]([O:37][CH3:38])=[O:36].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:38][O:37][C:35](=[O:36])[CH2:34][N:13]1[CH2:14][CH2:15][CH:10]([N:9]([CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:8][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58996965Bis-(3-methyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine

Product 1

HCID 67272256HCID 67272256, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of a solution of COMPOUND 249 (150 mg, 0.483 mmol) in CH2Cl2 (10 mL) and DIPEA (0.170 mL, 0.966 mmol) was added methyl bromoacetate (0.055 mL, 0.579 mmol), and the reaction mixture was stirred for 17 hr at room temperature. Saturated NaHCO3 (10 mL) was added to the reaction mixture, which was then extracted with CH2Cl2 (3×30 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by radial chromatography on silica gel (20:1:0.5 CH2Cl2:MeOH:NH4OH) to give {4-[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-piperidin-1-yl}-acetic acid methyl ester (154 mg, 83%). 1H NMR (CDCl3) δ 1.86-1.92 (m, 4H), 1.98-2.07 (m, 2H), 2.08 (s, 6H), 2.45-2.50 (m, 1H), 2.96-2.99 (m, 2H), 3.17 (s, 2H), 3.71 (s, 3H), 3.83 (s, 4H), 7.07 (dd, 2H, J=4.8, 7.5 Hz), 7.34 (d, 2H, J=7.5 Hz), 8.33 (d, 2H, J=4.8 Hz).

Workup

  1. extractionwas then extracted with CH2Cl2 (3×30 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by radial chromatography on silica gel (20:1:0.5 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-b4766f00c8964e0cbeb76fc93c83e66c
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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