Methyl iodide → 2-[4-(4-Methylamino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737155Notes

Reaction equation

HRID 737155 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31](N(CC)CC)C.CI>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][CH3:31])=[CH:27][CH:28]=2)[N:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 86616427(S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester2×

Product 1

HCID 578498582-[4-(4-Methylamino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[4-(4-amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (Compound 5050, 38 mg, 0.092 mmol) was dissolved in 3.5 mL of methylene chloride. To this solution was added triethylamine (12.8 μL, 0.092 mmol) followed by 6 μL (0.092 mmol) of methyl iodide. This solution was heated under reflux for 1 hour. It was evaporated and redissolved in 5 mL of DMF. The crude was purified using reverse phase HPLC to furnish the desired product. MS: 437.1 (M+H+).

Workup

  1. temperatureThis solution was heated
  2. temperatureunder reflux for 1 hour
  3. customIt was evaporated
  4. dissolutionredissolved in 5 mL of DMF
  5. customThe crude was purified

Sources & evidence

ORD record
ord-45186c9cd0f44544bf1588943e53eb63
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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