1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 121267850, compound

HRID 2205560Notes

Reaction equation

HRID 2205560 reaction equation
[NH2:1][C:2]1[C:11]([C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:15]=3[CH:16]=2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:22][C:23]1[CH:27]=[CH:26][O:25][C:24]=1[C:28](O)=[O:29].CCN=C=NCCCN(C)C>ClCCCl.CN(C1C=CN=CC=1)C>[NH2:1][C:2]1[C:11]([C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([NH:21][C:28]([C:24]4[O:25][CH:26]=[CH:27][C:23]=4[CH3:22])=[O:29])=[CH:17][C:15]=3[CH:16]=2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 781273-Methyl-2-furoic acidHCID 121267898HCID 121267898, compound

Product 1

HCID 121267850HCID 121267850, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To the mixture of methyl 6-amino-5-(5-amino-1-benzothien-2-yl)nicotinate (120 mg, 0.4 mmol, 1 eq) and 3-methylfuranylcarboxylic acid (50.4 mg, 1 eq) in 1,2-dichloroethane (3 mL) at 60° C. was added catalytic amount of DMAP (10 mg, 0.2 eq) and EDCI (92.2 mg, 1.2 eq). The reaction was stirred at that temperature for 2 h and then partitioned between EtOAc and saturated aq NaHCO3. The organic layer was further washed with brine and then dried with anhydrous sodium sulfate. The organic layer was decanted, concentrated, and the solid residue which was treated with ethyl acetate with stirring at room temperature for an hour. Methyl 6-amino-5-{5-[(3-methyl-2-furoyl)amino]-1-benzothien-2-yl}nicotinate was obtained upon filtration as a white solid in amount of 128 mg.

Workup

  1. custompartitioned between EtOAc and saturated aq NaHCO3
  2. washThe organic layer was further washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe organic layer was decanted
  5. concentrationconcentrated
  6. additionthe solid residue which was treated with ethyl acetate
  7. stirringwith stirring at room temperature for an hour

Sources & evidence

ORD record
ord-1dd422ac42934aea89312d20a99c004b
Source dataset
uspto-grants-2016_06
Patent number
US09371314B2

Reaction notes

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