1-Hydroxybenzotriazole → HCID 11650376, compound

HRID 552319Notes

Reaction equation

HRID 552319 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N:10]2[C:14]3=[N:15][C:16]([CH3:29])=[CH:17][C:18]([N:19]4[CH2:24][CH2:23][CH:22]([CH2:25][C:26](O)=[O:27])[CH2:21][CH2:20]4)=[C:13]3[C:12]([CH3:30])=[CH:11]2)=[C:5]([CH3:31])[CH:4]=1.Cl.[CH2:33]([O:35][C:36](=[O:46])[C@H:37]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[NH2:38])[CH3:34].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O.C(N(CC)CC)C>[CH2:33]([O:35][C:36](=[O:46])[C@@H:37]([NH:38][C:26](=[O:27])[CH2:25][CH:22]1[CH2:23][CH2:24][N:19]([C:18]2[CH:17]=[C:16]([CH3:29])[N:15]=[C:14]3[N:10]([C:6]4[C:5]([CH3:31])=[CH:4][C:3]([Br:2])=[CH:8][C:7]=4[CH3:9])[CH:11]=[C:12]([CH3:30])[C:13]=23)[CH2:20][CH2:21]1)[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH3:34]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67152535HCID 67152535, compound

Product 1

HCID 11650376HCID 11650376, compoundYield 58.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of {1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetic acid hydrochloride (300 mg), L-phenylalanine ethyl ester hydrochloride (204 mg), 1-hydroxybenzotriazole (108 mg) and triethylamine (90 mg) in DMF (3 mL) in an ice cooling bath was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (170 mg), and the mixture was stirred at room temperature for 4 hours. Water was added into the reaction mixture and the mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous NaHCO3 solution and brine, and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=1/1) to obtain (S)-2-(2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetylamino)-3-phenyl-propionic acid ethyl ester (222 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with a saturated aqueous NaHCO3 solution and brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=1/1)

Sources & evidence

ORD record
ord-71f6656257f5468ab7af66a7f80591d3
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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