Methylamine → HCID 57708177, compound

HRID 643716Notes

Reaction equation

HRID 643716 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:21])([CH3:20])[CH2:18][NH2:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:3][CH2:2]1.[CH2:27]([N:29]([CH2:32]C)CC)C.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:36].CN.[OH-].[Na+]>ClCCl.C(OCC)(=O)C>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:20])([CH3:21])[CH2:18][NH:19][C:27]([NH:29][CH3:32])=[O:36])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 6329MethylamineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 821294-Nitrophenyl chloroformateHCID 68615718HCID 68615718, compound

Product 1

HCID 57708177HCID 57708177, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropan-1-amine (Step K of Example 13, 177 mg, 0.469 mmol) and triethylamine (131 μL, 0.938 mmol) in dichloromethane (4 mL) was added p-nitrophenyl chloroformate (104 mg, 0.516 mmol) at room temperature. After stirring for 30 min, methylamine (40% aqueous solution, 3 mL) was added to the mixture and the whole was stirred for 2 h. To the resulting mixture was added ethyl acetate and 2 mol/L sodium hydroxide aqueous solution. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by HPLC (ODS, gradient elution with Acetonitrile 10.01% aq. NH3=4:96 to 96:4, by volume; flow rate 40 mL/min) to afford the title compound (34 mg, 17%) as an amorphous.

Workup

  1. stirringthe whole was stirred for 2 h
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by HPLC (ODS, gradient elution with Acetonitrile 10.01% aq. NH3=4:96 to 96:4, by volume; flow rate 40 mL/min)

Sources & evidence

ORD record
ord-7a60c0196f5a45d38896224a7c44494e
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

Loading…