Triethylamine → HCID 178495979, compound

HRID 1734028Notes

Reaction equation

HRID 1734028 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([N:16]=[C:17]([NH2:23])[NH:18][CH2:19][CH2:20][O:21][CH3:22])[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=1.[C:24]([O:28][C:29]([NH:31][CH2:32][C:33](O)=[O:34])=[O:30])([CH3:27])([CH3:26])[CH3:25].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C)C=O>[NH2:23][C:17](=[N:16][C:13]1[S:14][CH:15]=[C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][NH:3][C:33](=[O:34])[CH2:32][NH:31][C:29]([O:28][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:30])[CH:6]=2)[N:12]=1)[NH:18][CH2:19][CH2:20][O:21][CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178495975HCID 178495975, compound

Product 1

HCID 178495979HCID 178495979, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(3-aminomethylphenyl)-2-[[(amino)(2-methoxyethylamino)methylene]amino]thiazole dihydrochloride (3.9 g), N-(t-butoxycarbonyl)glycine (1.85 g), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (2.6 g) and triethylamine (2.3 g) in N,N-dimethylformamide (50 ml) was stirred for 7 hours with cooling on an ice bath. The solvent was removed under reduced pressure. The residue was dissolved in a mixture of water (80 ml) and tetrahydrofuran (20 ml), and the mixture was alkalized with 30% aqueous potassium carbonate solution. The mixture was extracted with ethyl acetate (200 ml) and the extract was dried with magnesium sulfate. The solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (20:1) to afford 2-[[(amino)(2-methoxyethylamino)methylene]amino]-4-(3-t-butoxycarbonylaminoacetylaminomethylphenyl)thiazole (1.65 g).

Workup

  1. temperaturewith cooling on an ice bath
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture of water (80 ml) and tetrahydrofuran (20 ml)
  4. extractionThe mixture was extracted with ethyl acetate (200 ml)
  5. dry with materialthe extract was dried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with a mixture of chloroform and methanol (20:1)

Sources & evidence

ORD record
ord-7a0af03f076941eab8987d29383ee785
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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