1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 90332500, compound

HRID 595592Notes

Reaction equation

HRID 595592 reaction equation
[NH2:1][C:2]1[C:16]([Br:17])=[CH:15][C:5]2[C:6]([C:12](O)=[O:13])=[C:7]([CH:9]3[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.C[CH2:19][N:20]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN.Cl>CN(C=O)C.CCN(CC)CC>[NH2:1][C:2]1[C:16]([Br:17])=[CH:15][C:5]2[C:6]([C:12]([NH:20][CH3:19])=[O:13])=[C:7]([CH:9]3[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 90332433HCID 90332433, compound

Product 1

HCID 90332500HCID 90332500, compoundYield 714.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 6-amino-5-bromo-2-cyclopropylbenzofuran-3-carboxylic acid (6.5 g, 22 mmol) in dry DMF (500 mL) were added EDCI (2.98 g, 2.4 mmol) and HOBT (6.33 g, 3.6 mmol). The reaction mixture was stirred at room temperature for 2 h, and then Et3N (20 mL) and MeNH2.HCl (7.3 g, 110 mmol) were added to the reaction mixture. After stirring for another 2 hours, the reaction mixture was concentrated in vacuum and Na2CO3 (a.q., 300 mL) was added to the mixture. The resulting solid was filtered to give the crude product, which was purified by column chromatography (DCM:MeOH=30:1) to give the product of 6-amino-5-bromo-2-cyclopropyl-N-methylbenzofuran-3-carboxamide (5.3 g, yield: 78%). 1H-NMR (400 MHz, CDCl3) δ 7.69 (s, 1H), 6.77 (s, 1H), 5.88 (s, 1H), 4.11 (s, 2H), 3.04 (d, J=4.8 Hz, 3H), 2.69˜2.73 (m, 1H), 1.10˜1.16 (m, 2H), 1.07˜1.09 (m, 2H). MS (M+H)+: 309/311.

Workup

  1. stirringAfter stirring for another 2 hours
  2. concentrationthe reaction mixture was concentrated in vacuum and Na2CO3 (a.q., 300 mL)
  3. additionwas added to the mixture
  4. filtrationThe resulting solid was filtered
  5. customto give the crude product, which
  6. customwas purified by column chromatography (DCM:MeOH=30:1)

Sources & evidence

ORD record
ord-9ed83e2cb4504fa7b36c48f782e7d0c1
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

Loading…