Water → HCID 9913574, compound

HRID 746469Notes

Reaction equation

HRID 746469 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[CH:25]=[CH:24][NH:23][C:18]4=[N:19][C:20]=3[O:21][CH3:22])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:28](Cl)(=[O:32])[C:29](Cl)=[O:30].[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.O>ClCCl>[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:25]([C:28](=[O:32])[C:29]([N:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)=[O:30])=[CH:24][NH:23][C:18]4=[N:19][C:20]=3[O:21][CH3:22])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 59747887HCID 59747887, compound

Product 1

HCID 9913574HCID 9913574, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[4-(4-Fluoro-benzyl)-piperidin-1-yl]-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanone (368 mg, 1 mmol) was dissolved in dry dichloromethane (5 mL). It was cooled in an ice-bath and oxalyl chloride (4.5 mL, 2 M solution in dichloromethane) was added. The mixture was stirred for 1 h at 0° C. and for another 4 h at room temperature. It was evaporated to dryness, redissolved in dichloromethane and treated with pyrrolidine (3 mmol). After stirring for 30 min, water was added and the product was extracted with dichloromethane (3×25 mL). The combined extracts were dried over sodium sulfate. After evaporation of the solvent, the product was purified via radial chromatography using chloroform-methanol (0-3% methanol) to yield 340 mg of the desired product. LCMS: 493, M+1.

Workup

  1. temperatureIt was cooled in an ice-bath
  2. customIt was evaporated to dryness
  3. dissolutionredissolved in dichloromethane
  4. stirringAfter stirring for 30 min
  5. extractionthe product was extracted with dichloromethane (3×25 mL)
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. customAfter evaporation of the solvent
  8. customthe product was purified via radial chromatography

Sources & evidence

ORD record
ord-2eb497728eb540acb3926923f60bbf7b
Source dataset
uspto-grants-2008_07
Patent number
US07393851B2

Reaction notes

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