Dimethylformamide → HCID 57901690, compound

HRID 1851389Notes

Reaction equation

HRID 1851389 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:24]([OH:26])=O)[N:6]2[CH2:21][O:22][CH3:23].C[N:28](C)C=O.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:24]([NH2:28])=[O:26])[N:6]2[CH2:21][O:22][CH3:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57901637HCID 57901637, compound

Product 1

HCID 57901690HCID 57901690, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-fluoro-1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.41 g), 1H-1,2,3-benzotriazol-1-ol-ammonia complex (0.21 g) and N,N-dimethylformamide (15 ml) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.26 g) at 4° C., and the mixture was stirred at room temperature for 2 days. The reaction solution was diluted with ethyl acetate, washed with water, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (0.41 g, yield 100%) as pale-yellow needle crystals.

Workup

  1. washwashed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc599b409a484c50b1da2fa51fd6555b
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…