Triethylamine → HCID 57708173, compound

HRID 643721Notes

Reaction equation

HRID 643721 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][C:18]([CH3:21])([NH2:20])[CH3:19])(=[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.C([N:29]([CH2:32]C)CC)C.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:36].[OH-].[NH4+]>ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][C:18]([NH:20][C:32]([NH2:29])=[O:36])([CH3:19])[CH3:21])(=[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

6

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 821294-Nitrophenyl chloroformateHCID 68615607HCID 68615607, compound

Product 1

HCID 57708173HCID 57708173, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropan-2-amine (step G, 38 mg, 0.1 mmol) in dichloromethane (1.5 mL) were added triethylamine (28 μL, 0.2 mmol) and 4-nitrophenyl chloroformate (24 mg, 0.12 mmol) at 0° C. The mixture was stirred for 4 h at room temperature. To the resulting mixture was added ammonium hydroxide solution (25% in water; 20 μL, 0.12 mmol) and stirred continue to 20 h. The reaction was quenched by addition of saturated sodium 6 bicarbonate aqueous solution (10 mL) and water (10 mL). The organic phase was separated and the aqueous layer was extracted with dichloromethane (10 mL×2). The combined organic layer was washed with water (20 mL×4), brine (10 mL) and dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel TLC eluting with dichloromethane/methanol (10/1) to afford 16 mg (38%) of the title compound.

Workup

  1. stirringstirred
  2. waitcontinue to 20 h
  3. customThe reaction was quenched by addition of saturated sodium 6 bicarbonate aqueous solution (10 mL) and water (10 mL)
  4. customThe organic phase was separated
  5. extractionthe aqueous layer was extracted with dichloromethane (10 mL×2)
  6. washThe combined organic layer was washed with water (20 mL×4), brine (10 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel TLC
  11. washeluting with dichloromethane/methanol (10/1)

Sources & evidence

ORD record
ord-0c931750d6e04040854a2342451fe2cb
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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