Dimethylformamide → HCID 57901665, compound

HRID 1851495Notes

Reaction equation

HRID 1851495 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([OH:20])=O)=[CH:14]2)=[O:7].C[N:22](C)C=O.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([NH2:22])=[O:20])=[CH:14]2)=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57901652HCID 57901652, compound

Product 1

HCID 57901665HCID 57901665, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 7-[(2-thienylcarbonyl)amino]-1H-indole-2-carboxylic acid (100 mg), 1H-1,2,3-benzotriazol-1-ol-ammonia complex (63 mg) and N,N-dimethylformamide (5 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (80 mg) at 4° C., and the mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with ethyl acetate-hexane to give the title compound (97 mg, yield 98%) as pale-brown crystals. melting point 289-290° C.

Workup

  1. washwashed with aqueous sodium hydrogencarbonate solution, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-909aeafcf6ec418d8c60e0e83e35cfad
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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