4-Methylmorpholine → N-(2-oxo-2-{[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]amino}ethyl)-4-phenoxybenzamide

HRID 1790086Notes

Reaction equation

HRID 1790086 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[N:9][N:10]2[CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:4].[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36]C(O)=O)=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25]C=1.Cl.C(N=C=NC(C)(C)CC)C.[OH:51]N1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[O:4]=[C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[N:9][N:10]2[CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)[CH2:2][NH:1][C:36](=[O:51])[C:33]1[CH:32]=[CH:31][C:30]([O:29][C:22]2[CH:23]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 810334-Benzyloxyphenylacetic acidHCID 220366182-amino-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-acetamideHCID 22992078Ethyldimethylpropylcarbodiimide hydrochloride

Product 1

HCID 11443083N-(2-oxo-2-{[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]amino}ethyl)-4-phenoxybenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-acetamide (HCl salt, 0.0600 g, 0.186 mmol), (4-benzyloxy-phenyl)-acetic acid (0.0470 g, 0.190 mmol), ethyldimethylpropylcarbodiimide hydrochloride (0.0430 g, 0.225 mmol), N-hydroxybenzotriazole (0.0300 g, 0.222 mmol), N-methyl morpholine (0.0460 g, 0.455 mmol) in 2 mL of DMF was stirred for 6 hours. The mixture was concentrated under reduced pressure, the residue dissolved in 1.5 mL of a 1:1 mixture of DMSO/MeOH and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.62 (m, 4H), 2.44 (m, 4H), 2.87 (t, 2H, J=6.78), 2.95 (s, 2H), 4.20 (d, 2H, J=5.76), 4.48 (t, 2H, J=6.78), 6.99–7.47 (m, 9H), 7.65 (m, 1H), 7.96 (m, 2H), 8.27 (m, 1H), 8.83 (m, 1H), 10.13 (s, 1H); MS (DCI/NH3) m/z 484 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in 1.5 mL of a 1:1 mixture of DMSO/MeOH
  3. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-a37a0b99e6e54e88b3ec6ab23609e14e
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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