Benzylamine → HCID 86725362, compound

HRID 2172838Notes

Reaction equation

HRID 2172838 reaction equation
[O:1]=[C:2]1[C:6](=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16](O)=[O:17])[CH:9]=2)[S:5][C:4](=[S:19])[N:3]1[NH:20][C:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[S:23](=[O:31])(=[O:30])[N:22]=1.[CH2:32](N)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O[N:41]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[O:1]=[C:2]1[C:6](=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH:15]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:16]([NH2:41])=[O:17])[CH:9]=2)[S:5][C:4](=[S:19])[N:3]1[NH:20][C:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[S:23](=[O:31])(=[O:30])[N:22]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 78077574HCID 78077574, compound

Product 1

HCID 86725362HCID 86725362, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[(4-oxo-5-(3-(carboxymethyloxy)benzylidene)-2-thioxothiazolidin-3-yl)amino]-1,2-benzothiazole 1,1-dioxide (34 mg) obtained in Example 174 and benzylamine (8 mg) in N,N-dimethylformamide (1 ml) were added 1-hydroxybenzotriazole (10 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (14 mg) with stirring under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice water (20 ml), and the mixture was extracted with ethyl acetate (30 ml). The extract was washed successively with 0.5M aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 3-[(4-oxo-5-(3-(benzyl aminocarbonylmethyloxy)benzylidene)-2-thioxothiazolidin-3-yl)amino]-1,2-benzothiazole 1,1-dioxide (34 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted with ethyl acetate (30 ml)
  3. washThe extract was washed successively with 0.5M aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5dcbb1550e14da3b6d44f5b71b5b739
Source dataset
uspto-grants-2015_06
Patent number
US09056862B2

Reaction notes

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