Ammonia → HCID 178513688, compound

HRID 274981Notes

Reaction equation

HRID 274981 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([NH:12][CH:13]([CH2:25][C:26]2[CH:34]=[CH:33][C:29]3[NH:30][CH:31]=[N:32][C:28]=3[CH:27]=2)[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=O)[CH2:18][CH2:17]2)=[O:15])(=[O:11])=[O:10])=[CH:4][C:3]=1[Cl:35].C(N1C=CN=C1)([N:38]1C=CN=C1)=O.N>CN(C)C=O>[NH2:1][C:2]1[C:3]([Cl:35])=[CH:4][C:5]([S:9]([NH:12][CH:13]([CH2:25][C:26]2[CH:34]=[CH:33][C:29]3[NH:30][CH:31]=[N:32][C:28]=3[CH:27]=2)[C:14]([N:16]2[CH2:17][CH2:18][CH:19]([C:22]([NH2:38])=[O:24])[CH2:20][CH2:21]2)=[O:15])(=[O:11])=[O:10])=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 178507842HCID 178507842, compound

Product 1

HCID 178513688HCID 178513688, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

540 mg (1 mMol) of 4-amino-N-[1-(1H-benzimidazol-5-yl-methyl)-2-(4-carboxy-piperidin-1-yl)-2-oxo-ethyl]-3,5-dichloro-benzenesulphonamide are dissolved in 10 ml of absolute dimethylformamide and combined, with stirring, with 180 mg (1.1 mMol) of carbonyldiimidazole. After about one hour 2 ml of ethanolic ammonia solution are added dropwise and the mixture is stirred for a further 12 hours. It is then evaporated down, the residue is mixed with water and extracted twice with ethyl acetate. The organic phase is washed twice with aqueous saline solution, dried with sodium sulphate and evaporated down. The residue is purified over a silica gel column, the evaporated eluate is triturated with ether and suction filtered.

Workup

  1. customIt is then evaporated down
  2. additionthe residue is mixed with water
  3. extractionextracted twice with ethyl acetate
  4. washThe organic phase is washed twice with aqueous saline solution
  5. dry with materialdried with sodium sulphate
  6. customevaporated down
  7. customThe residue is purified over a silica gel column
  8. customthe evaporated eluate is triturated with ether and suction
  9. filtrationfiltered

Sources & evidence

ORD record
ord-36d67faab69943d59baf86368fc9bc9b
Source dataset
uspto-grants-1995_02
Patent number
US05391556

Reaction notes

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