Thiophene-3-carboxylic acid → HCID 59830435, compound

HRID 1362931Notes

Reaction equation

HRID 1362931 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([C:18]([NH:20][NH2:21])=[O:19])[NH:15][C:12]2=[CH:13][N:14]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[S:52]1[CH:56]=[CH:55][C:54]([C:57](O)=[O:58])=[CH:53]1>CN(C=O)C.C(OCC)(=O)C>[Cl:8][C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([C:18]([NH:20][NH:21][C:57]([C:54]3[CH:55]=[CH:56][S:52][CH:53]=3)=[O:58])=[O:19])[NH:15][C:12]2=[CH:13][N:14]=1

Participants

8

Reactant 5

HCID 6918Thiophene-3-carboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 86624323HCID 86624323, compound

Product 1

HCID 59830435HCID 59830435, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid hydrazide trifluoroacetic acid salt (Preparation 10—route 1, 0.110 g, 0.34 mmol) in DMF (3 mL) was added DIPEA (170.0 μL, 1.02 mmol). To the stirred solution, HOBt (0.046 g, 0.34 mmol), EDCI (0.078 g, 0.41 mmol), DIPEA (120.0 μL, 0.68 mmol) and thiophene-3-carboxylic acid (0.044 g, 0.34 mmol) were added. The reaction mixture was stirred at rt for 16 h and then concentrated in vacuo to give an oil. On addition of ethyl acetate to the oil, a solid precipitated. The solid was filtered and dried to give the title compound. m/z (ES+)=321 [M+H]+; RT=2.84 min.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give an oil
  3. customa solid precipitated
  4. filtrationThe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-a71aa0d9dc2c4540bcd9d8d3e5478f1e
Source dataset
uspto-grants-2011_02
Patent number
US07884112B2

Reaction notes

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