1,1'-Carbonyldiimidazole → HCID 67894696, compound

HRID 846611

Reaction equation

HRID 846611 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[OH:27][C:28]1([CH2:36][NH2:37])[CH:33]2[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]2)[CH2:29]1>O1CCCC1>[OH2:3].[OH:27][C:28]1([CH2:36][NH:37][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:14][CH:13]=2)[CH:33]2[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]2)[CH2:29]1.[OH:27][C:28]1([CH2:36][NH:37][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][CH:8]=2)[CH:33]2[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]2)[CH2:29]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2506534-(Methylsulfonamido)benzoic acidHCID 147899783-(Aminomethyl)quinuclidin-3-ol

Product 1

HCID 67894696HCID 67894696, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution/suspension of 4-[(methanesufonyl)amino]benzoic acid (1.62 g, 7.5 mmol) in anhydrous tetrahydrofuran (6 ml) under nitrogen was treated with 1,1'-carbonyldiimidazole (1.38 g, 8.5 mmol), stirred for 45 minutes, and degassed under a stream of nitrogen over 15 minutes. A solution of 3-hydroxy-1-azabicyclo[2.2.2]oct-3-ylmethanamine (1.56 g, 10 mmol) in anhydrous tetrahydrofuran (6 mL) was added, and the mixture soon became cloudy. After 18 hours at room temperature and 90 minutes at 50° C. the mixture was concentrated in vacuo and the residue was triturated from acetonitrile. The foamy solid thus obtained was filtered through alumina (eluted with 1:1 methanol/tetrahydrofuran) and the filtrate was concentrated in vacuo and recrystallized from 2-propanol/ether to afford 1.92 g (71%) of the title compound as a hygroscopic voluminous colorless solid (water soluble); mp 123°-125° C. (foam).

Workup

  1. customdegassed under a stream of nitrogen over 15 minutes
  2. waitAfter 18 hours at room temperature
  3. concentration90 minutes at 50° C. the mixture was concentrated in vacuo
  4. customthe residue was triturated from acetonitrile
  5. customThe foamy solid thus obtained
  6. filtrationwas filtered through alumina (eluted with 1:1 methanol/tetrahydrofuran)
  7. concentrationthe filtrate was concentrated in vacuo
  8. customrecrystallized from 2-propanol/ether

Sources & evidence

ORD record
ord-ee0fd5ad773145a4b10a3650b6265a80
Source dataset
uspto-grants-1992_08
Patent number
US05137895

Linked notes

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