Dimethylformamide → HCID 23433066, compound

HRID 2121354Notes

Reaction equation

HRID 2121354 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=N1.[CH2:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH3:24].[CH3:30]N(C)CCCN=C=NCC.CN(C)[CH:43]=[O:44]>>[NH2:1][C:2]1[C:11]([NH:12][C:43]([C:21]2[CH:20]=[CH:19][C:18]3[N:14]([CH2:24][CH2:23][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH:30]=[N:16][C:17]=3[CH:22]=2)=[O:44])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5718252,3-Diaminobenzoic acid methyl ester

Product 1

HCID 23433066HCID 23433066, compound

Procedure

To 3.3 g (9.9 mmol) of the product 4b in 100 ml of anhydrous dimethylformamide at room temperature were successively added 1.6 g (9.9 mmol) of methyl 2,3-diaminobenzoate, 0.44 g (3.3 mmol) of N-hydroxybenzotriazole (HOBT) and 6.2 ml (44.4 mmol) of triethylamine. Then, at 15° C., 1.9 g (9.9 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDC) were added in portions. The mixture was stirred at room temperature for 16 hours. The reaction mixture was then concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The aqueous phase was separated off, made alkaline with aqueous sodium bicarbonate solution and extracted with ethyl acetate. This organic phase was separated off, treated with active carbon, filtered, dried and concentrated in vacuo. 1.5 g of the product were obtained as an isomer mixture.

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. customThe aqueous phase was separated off
  5. extractionextracted with ethyl acetate
  6. customThis organic phase was separated off
  7. additiontreated with active carbon
  8. filtrationfiltered
  9. customdried
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e35fc2cea1a472f80d0900ea0b2695a
Source dataset
uspto-grants-2004_02
Patent number
US06696437B1

Reaction notes

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