4-Methylmorpholine → 2-(4-bromophenyl)-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-6-yl]acetamide

HRID 1790139Notes

Reaction equation

HRID 1790139 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[CH:10]=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26](O)=[O:27])=[CH:21][CH:20]=1.Cl.C(N=C=NC(C)(C)CC)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([NH:17][C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[N:9][N:8]3[CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:12][CH:13]=2)=[O:27])=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 74654Benzeneacetic acid, 4-bromo-HCID 757711-HydroxybenzotriazoleHCID 112762881-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-6-ylamineHCID 22992078Ethyldimethylpropylcarbodiimide hydrochloride

Product 1

HCID 220365732-(4-bromophenyl)-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-6-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine (480 mg, 2.09 mmol), (4-bromo-phenyl)-acetic acid (449 mg, 2.09 mmol), ethyldimethylpropylcarbodiimide hydrochloride (470 mg, 2.23 mmol), N-hydroxybenzotriazole (330 mg, 2.44 mmol), N-methyl morpholine (500 mg, 5.00 mmol) in 20 mL of DMF was shaken for 6 hours, concentrated under reduced pressure and the residue purified by preparative reverse-phase HPLC. 1H NMR (500 MHz, DMSO-D6) δ ppm 1.82 (m, 2 H), 1.98 (m, 2 H), 3.01 (m, 2 H), 3.50 (m, 2 H), 3.79 (m, 4 H), 4.66 (t, J=6.24 Hz, 2 H), 7.12 (m, 1 H), 7.32 (m, 2 H), 7.54 (m, 2 H), 7.72 (m, 1 H), 8.08 (s, 1 H), 8.25 (s, 1 H), 10.44 (s, 1 H); MS (DCI/NH3) m/z 429 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-06dbbfb91b364cc0afe00fc3defc95f4
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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