Ethyl Acetate → 2-(1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)acetamide

HRID 2169429Notes

Reaction equation

HRID 2169429 reaction equation
[N:1]1([C:10]2([CH2:15][C:16]([OH:18])=O)[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([N:22](CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(OCC)(=O)C>CN(C)C=O.CCCCCC.O>[N:1]1([C:10]2([CH2:15][C:16]([NH2:22])=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86726059(1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetic acid

Product 1

HCID 867260602-(1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)acetamideYield 63.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of (1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetic acid (397) (2.7 g, 11.05 mmol) in dimethylformamide (60 mL) was added N,N-diisopropylethylamine (5.8 mL, 33.16 mmol) followed by (NH4)2CO3 (5.2 g, 33.16 mmol) and HATU (6.3 g, 16.58 mmol) and stirring was continued for 1 h at room temperature (TLC, 50% ethyl acetate in hexane, Rf=0.5), Water (200 mL) was added and the mixture was extracted with ethyl acetate (2×200 mL), organic part was washed with water (2×100 mL) and brine (2×100 mL). The organic phase was thereafter dried and concentrated. The crude product was purified by Combi-Flash column chromatography (eluted at 30-40% ethyl acetate in hexane) to get 2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)acetamide (398) (1.7 g, 63%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×200 mL), organic part
  2. washwas washed with water (2×100 mL) and brine (2×100 mL)
  3. customThe organic phase was thereafter dried
  4. concentrationconcentrated
  5. customThe crude product was purified by Combi-Flash column chromatography (eluted at 30-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-35ee603c50d3404cbb251a8ee95aeefb
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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