Water → 7-Chloro-N-(phenylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

HRID 1821832Notes

Reaction equation

HRID 1821832 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([OH:13])=O)[NH:8][C:7]=12.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C)C=O>[CH2:26]([NH:33][C:11]([C:9]1[NH:8][C:7]2=[C:2]([Cl:1])[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=1)=[O:13])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 768529167-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Product 1

HCID 578935017-Chloro-N-(phenylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamideYield 27.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Reference Example 1) (0.10 g, 0.51 mmol) and 1,1′-carbonyldiimidazole (0.09 g, 0.53 mmol) in N,N-dimethylformamide (3.4 mL) was stirred at 50° C. for 1 h. To the stirring solution was added benzylamine (0.11 mL, 1.02 mmol) and the reaction mixture was stirred at 65° C. until the reaction was complete by TLC analysis. The crude reaction mixture was poured into rapidly stirring water, and extracted with ethyl acetate (3×). The combined organic extracts were washed with water (3×) and saturated NH4Cl, and dried over Na2SO4. The organic extract was filtered and concentrated to provide N-benzyl-7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (0.04 g, 0.14 mmol, 27%) as an off-white solid: mp 217-220° C.; 1H NMR (300 MHz, CDCl3) δ4.70 (2H, d, J=5.7 Hz), 6.45-6.61 (1H, m), 6.85 (1H, s), 7.31-7.39 (5H, m), 7.47 (1H, d, J=5.7 Hz), 8.06 (1H, d, J=5.7 Hz), 9.55 (1H, br s); APCI MS m/z 286 [C15H12ClN3O+H]+; HPLC (Method A) >99% (AUC), tR=16.3 min.

Workup

  1. stirringthe reaction mixture was stirred at 65° C. until the reaction
  2. customThe crude reaction mixture
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic extracts were washed with water (3×) and saturated NH4Cl
  5. dry with materialdried over Na2SO4
  6. extractionThe organic extract
  7. filtrationwas filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-71a4b0bd27a0400e8006b7d94e401fd7
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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