Triethylamine → N-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-dimethylamino-acetamide

HRID 1515855Notes

Reaction equation

HRID 1515855 reaction equation
Cl.[CH:2]1([CH2:7][CH:8]([C:19]2[NH:28][C:22]3=[N:23][CH:24]=[C:25]([NH2:27])[CH:26]=[C:21]3[CH:20]=2)[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.[CH3:30][N:31]([CH3:36])[CH2:32][C:33](O)=[O:34].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl.CN(C)C=O>[CH:2]1([CH2:7][CH:8]([C:19]2[NH:28][C:22]3=[N:23][CH:24]=[C:25]([NH:27][C:33](=[O:34])[CH2:32][N:31]([CH3:36])[CH3:30])[CH:26]=[C:21]3[CH:20]=2)[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 75605N,N-Dimethylglycine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67229247HCID 67229247, compound

Product 1

HCID 67228714N-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-dimethylamino-acetamideYield 16%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylamine hydrochloride (0.25 g, 0.6 mmol), N,N-dimethyl glycine hydrochloride (0.13 g, 0.9 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.23 g, 1.2 mmol), 1-hydroxybenzotriazole (0.16 g, 1.2 mmol), 4-dimethylaminopyridine (7.3 mg, 0.06 mmol), triethylamine (0.3 g, 3.0 mmol) and N,N-dimethylformamide (2 mL) in dichloromethane (5 mL) was stirred for 12 h at room temperature. The reaction was quenched with water (5 mL), extracted with ethyl acetate (2×10 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) to afford N-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-dimethylamino-acetamide (45 mg, 16%): LC/MS m/e calcd for C25H32N4O3S [M+H]+ 469.62, observed 469.1; 1H NMR (400 MHz, CDCl3) δ ppm 1.17 (m, 2H), 1.45 (m, 2H), 1.53-1.83 (m, 5H, H), 2.10 (m, 1H), 2.24 (m, 1H), 2.44 (s, 6H), 3.01 (s, 3H), 3.17 (s, 2H), 4.26 (t, J=7.8 Hz, 1H), 6.33 (s, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.84 (d, J=8.3 Hz, 2H), 8.17 (d, J=2.1 Hz, 1H), 8.28 (d, J=2.1 Hz, 1H), 9.19 (s, 1H), 10.96 (s, 1H).

Workup

  1. customThe reaction was quenched with water (5 mL)
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-3bf9ef9e816047b4b7b62093be23ac4a
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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