1,1'-Carbonyldiimidazole → HCID 9931208, compound

HRID 2254614Notes

Reaction equation

HRID 2254614 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH2:13][C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:32][CH:33]1[CH:38]2[CH2:39][CH2:40][N:35]([CH2:36][CH2:37]2)[CH2:34]1>O1CCCC1>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:32][CH:33]2[CH:38]3[CH2:39][CH2:40][N:35]([CH2:36][CH2:37]3)[CH2:34]2)=[O:8])=[C:4]([O:12][CH2:13][C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1232383-AminoquinuclidineHCID 19742825HCID 19742825, compound

Product 1

HCID 9931208HCID 9931208, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 4-amino-5-chloro-2-[(2-methylthiazol-4-yl)methoxy]benzoic acid (1.54 g, 5 mmoles) in anhydrous tetrahydrofuran (5 ml) was treated with 1,1'-carbonyldiimidazole (0.89 g, 5.5 mmoles), stirred at room temperature for 90 minutes, then added to a cooled (0° C.) solution of 3-aminoquinuclidine (from 6 mmoles of dihydrochloride salt and 12 mmoles of 25% sodium methoxide/methanol) in anhydrous tetrahydrofuran (5 ml) under nitogen. After 3 hours at room temperature and one hour at 60° C., the solution was concentrated in vacuo and partitioned between methylene chloride (50 ml) and 1.5N sodium hydroxide (20 ml). The organic layer was washed with 1.5N sodium hydroxide (20 ml), saturated sodium bicarbonate (20 ml), and brine (20 ml), dried (Na2SO4), and concentrated in vacuo. Filtration through alumina (eluted with 10% methanol/methylene chloride) provided 1.35 g (66%) of a colorless foam.

Workup

  1. additionadded to
  2. waitAfter 3 hours at room temperature
  3. concentrationone hour at 60° C., the solution was concentrated in vacuo
  4. custompartitioned between methylene chloride (50 ml) and 1.5N sodium hydroxide (20 ml)
  5. washThe organic layer was washed with 1.5N sodium hydroxide (20 ml), saturated sodium bicarbonate (20 ml), and brine (20 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. filtrationFiltration through alumina (eluted with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-7f49c768904248f2b53b95bfee989676
Source dataset
uspto-grants-1993_08
Patent number
US05236931

Reaction notes

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