Sodium Bicarbonate → HCID 68463791, compound

HRID 2239118Notes

Reaction equation

HRID 2239118 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH:8]2[S:12][C:11]([C:13]3[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][C:16]=4[N:22]([S:27]([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)(=[O:29])=[O:28])CC(O)=O)=[N:10][CH2:9]2)[CH2:3][CH2:2]1.Cl.C[N:37](C)[CH2:38][CH2:39]CN=C=NCC.C(=O)([O-])[OH:48].[Na+]>CN(C)C=O>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH:8]2[S:12][C:11]([C:13]3[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][C:16]=4[N:22]([S:27]([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)(=[O:28])=[O:29])[C:39](=[O:48])[CH2:38][NH2:37])=[N:10][CH2:9]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59136008HCID 59136008, compound

Product 1

HCID 68463791HCID 68463791, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-(2-thienylsulfonyl)glycine (60 mg) in N,N-dimethylformamide (5 mL) were added 1H-1,2,3-benzotriazol-1-ol-ammonia complex (30 mg) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (35 mg) under ice-cooling, and the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO4), and concentrated. The residue was recrystallized from a mixed solvent of ethyl acetate-hexane to give the title compound (43 mg, yield 71%) as white crystals. MS: 520 (MH+).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was recrystallized from a mixed solvent of ethyl acetate-hexane

Sources & evidence

ORD record
ord-5b3c1d138d28436da6759de28c533514
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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