Dimethylformamide → HCID 22048117, compound

HRID 1759756Notes

Reaction equation

HRID 1759756 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[CH2:4][CH2:5]CN=C=NCC.[N+:13]([C:16]1[CH:26]=[CH:25][C:19](OCC(O)=O)=[CH:18][CH:17]=1)([O-:15])=[O:14].[CH:27]([N:30]1[CH2:35]CNCC1)([CH3:29])[CH3:28].[OH:36]N1C2C=CC=CC=2N=N1.CN([CH:49]=[O:50])C>>[CH:27]([N:30]1[CH2:5][CH2:4][N:3]([CH2:2][O:36][C:49]([C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:26][CH:25]=2)=[O:50])[CH2:12][CH2:35]1)([CH3:29])[CH3:28]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 15720(4-Nitrophenoxy)acetic acidHCID 757711-HydroxybenzotriazoleHCID 780131-IsopropylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22048117HCID 22048117, compoundYield 22%

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.14 g, 11.0 mmol) was added to a solution of 4-nitrophenoxyacetic acid (obtained as described in J. Med. Chem., 1984, 27, 967-78; 2.0 g, 10.0 mmol), 4-isopropylpiperazine (2.56 g, 20.0 mmol) and 1-hydroxybenzotriazol (2.06 g, 15.0 mmol) in DMF (50 ml) at 0° C. The mixture was stirred for 16 hours and volatile material was removed by evaporation. Water (50 ml) was added and the mixture was extracted with ethyl acetate (3×100 ml). The extracts were dried and concentrated by evaporation to give the product as a yellow solid (600 mg, 22%). NNR: 1.0 (d, 6H), 2.4 (m, 4H), 2.7 (m, 1H), 3.4 (m, 4H), 5.0 (s, 2H), 7.1 (d, 2H), 8.2 (d, 2H); MS (MH+): 307.9.

Workup

  1. customvolatile material was removed by evaporation
  2. additionWater (50 ml) was added
  3. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  4. customThe extracts were dried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0e5a91b908284a51845aa8707a03de16
Source dataset
uspto-grants-2005_01
Patent number
US06838464B2

Reaction notes

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