Methyl iodide → N-([1-[(7-chlorothieno[3,2-b]pyridin-2-yl)carbonyl]pyrrolidin-3-yl}methyl)-N-methylamine

HRID 985240Notes

Reaction equation

HRID 985240 reaction equation
[H-].[Na+].CI.[Cl:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[C:13]([C:15]([N:17]3[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][C:24](=O)OC(C)(C)C)[CH2:18]3)=[O:16])[S:14][C:7]=12>C1COCC1>[Cl:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[C:13]([C:15]([N:17]3[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][CH3:24])[CH2:18]3)=[O:16])[S:14][C:7]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20767942tert-Butyl {1-[(7-chlorothieno[3,2-b]pyridin-2-yl)carbonyl]pyrrolidin-3-yl}methylcarbamate

Product 1

HCID 22143574N-([1-[(7-chlorothieno[3,2-b]pyridin-2-yl)carbonyl]pyrrolidin-3-yl}methyl)-N-methylamineYield 134.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (0.033 g, 0.82 mmole) and CH3I (0.064 ml, 1.02 mmole) were added to a solution of tert-butyl {1-[(7-chlorothieno[3,2-b]pyridin-2-yl)carbonyl]pyrrolidin-3-yl}methyl-carbamate 43 (0.271 g, 0.68 mmole) in THF at 0° C. The reaction mixture was stirred and warmed to room temperature overnight and partitioned between H2O (50 ml) and EtOAc (2×50 ml). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 0-2% CH3OH in CH2Cl2 to give a yellow solid (0.283 g, 82%). 1H NMR (300 MHz, CDCl3) δ8.62 (1H, d, J=5.1 Hz), 7.85 (1H, s), 7.34 (1H, d, J=5.1 Hz), 4.72 (1H, s), 3.99 (1H, m), 3.77 (2H, m), 3.50 (1H, m), 3.19 (2H, m), 2.88 (3H, d, J=12.06 Hz), 2.62 (1H, m), 2.14 (1H, m), 1.83 (1H, m); ESIMS (MH+): 310.10.

Workup

  1. custompartitioned between H2O (50 ml) and EtOAc (2×50 ml)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography
  5. washeluting with 0-2% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-6ac94d2f48a44b32a912ba33289cb76c
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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