Triethylamine → HCID 53762130, compound

HRID 1953256Notes

Reaction equation

HRID 1953256 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:32]=[CH:31][C:14]3[N:15]([CH2:27][C:28](O)=[O:29])[C:16]([CH2:18][C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)=[N:17][C:13]=3[CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:34]([O:36][C:37](=[O:40])[CH2:38][NH2:39])[CH3:35].C(N(CC)CC)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[C:1]1([S:7]([NH:10][C:11]2[CH:32]=[CH:31][C:14]3[N:15]([CH2:27][C:28]([NH:39][CH2:38][C:37]([O:36][CH2:34][CH3:35])=[O:40])=[O:29])[C:16]([CH2:18][C:19]4[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=4)=[N:17][C:13]=3[CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 53634320HCID 53634320, compound

Product 1

HCID 53762130HCID 53762130, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.7 g (6.1 mmol) of 4-[(5-benzenesulphonylamino-1-carboxymethyl-1H-benzimidazol-2-yl)-methyl]-benzonitrile, 0.85 g (6.1 mmol) of glycine-ethyl ester-hydrochloride and 1.5 g (15 mmol) of triethylamine are dissolved in 80 ml dimethylformamide and after the addition of 2.4 g (7.5 mmol) of O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluroniumtetrafluoroborate the mixture is stirred for 16 hours at ambient temperature. The solvent is evaporated off, the residue chromatographed on silica gel and eluted with methylene chloride/ethanol 99:1 and 98:2. The desired fractions are concentrated by evaporation, the residue is triturated with ether, suction filtered and dried.

Workup

  1. customThe solvent is evaporated off
  2. customthe residue chromatographed on silica gel
  3. washeluted with methylene chloride/ethanol 99:1 and 98:2
  4. concentrationThe desired fractions are concentrated by evaporation
  5. customthe residue is triturated with ether, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-9357b797d9a3445f8b72036a68dc18dc
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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