Dimethylformamide → HCID 57901685, compound

HRID 1851461Notes

Reaction equation

HRID 1851461 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:20]=2[NH:19][C:18]([C:21](O)=[O:22])=[CH:17]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[N:25](C)C=O.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:20]=2[NH:19][C:18]([C:21]([NH2:25])=[O:22])=[CH:17]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57901852HCID 57901852, compound

Product 1

HCID 57901685HCID 57901685, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 7-{[(4-methylphenyl)sulfonyl]amino}-1H-indole-2-carboxylic acid (105 mg), 1H-1,2,3-benzotriazol-1-ol-ammonia complex (58 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 5 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 (69 mg, yield 66%) as pale-yellow crystals. melting point 312-313° 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-ce4aef2f453d4177b442397784b5e9c3
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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