Dimethylformamide → HCID 23582475, compound

HRID 1393899Notes

Reaction equation

HRID 1393899 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[C:14]4[CH:20]=[C:19]([C:21](O)=[O:22])[NH:18][C:15]4=[CH:16][N:17]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C=O)C.[CH2:29]([N:31](CC)[CH2:32][CH3:33])[CH3:30].N1CCCC1>C(Cl)Cl>[CH:1]1([N:6]2[CH2:7][CH2:8][N:9]([C:12]3[CH:13]=[C:14]4[CH:20]=[C:19]([C:21]([N:31]5[CH2:32][CH2:33][CH2:30][CH2:29]5)=[O:22])[NH:18][C:15]4=[CH:16][N:17]=3)[CH2:10][CH2:11]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 31268PyrrolidineHCID 69024629HCID 69024629, compound

Product 1

HCID 23582475HCID 23582475, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.46 g (1.31 mmol) 5-(4-cyclopentyl-piperazin-1-yl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid 0.56 mL (6.6 mmol) oxalylchloride and 0.03 mL DMF in 30 mL DCM was stirred at room temperature for 1 h and evaporated to dryness. An aliquot containing 0.054 mmol of the intermediately built acid chloride was treated with 27 mg (0.27 mmol) triethylamine and 11.6 mg (0.16 mmol) pyrrolidine in 2 mL DCM during 16 h at room temperature. After evaporation of all volatiles the residue was taken up in a mixture of DMF/methanol/water/NEt3 and subjected to preparative HPLC purification on reversed phase eluting with a acetonitrile/water (0.05% NEt3) gradient. After evaporation of the product fractions 4.1 mg (14%) of the title compound was obtained.

Workup

  1. customevaporated to dryness
  2. additionAn aliquot containing 0.054 mmol of the intermediately built acid chloride
  3. customAfter evaporation of all volatiles the residue
  4. additionwas taken up in a mixture of DMF/methanol/water/NEt3
  5. customsubjected to preparative HPLC purification on reversed phase
  6. washeluting with a acetonitrile/water (0.05% NEt3) gradient
  7. customAfter evaporation of the product fractions 4.1 mg (14%) of the title compound
  8. customwas obtained

Sources & evidence

ORD record
ord-29e225cc51664f20bf72ba28a6e286cc
Source dataset
uspto-grants-2008_03
Patent number
US07348323B2

Reaction notes

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