4-Methylmorpholine → 2-(4-phenoxyphenyl)-N-[2-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-yl]acetamide

HRID 1825827Notes

Reaction equation

HRID 1825827 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][C:13]([NH2:17])=[CH:14]3)=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([OH:35])=O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21]C=1.Cl.C(N=C=NC(C)(C)CC)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[O:25]([C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:17][C:13]2[CH:12]=[CH:11][C:10]3[C:15](=[CH:16][N:8]([CH2:7][CH2:6][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[N:9]=3)[CH:14]=2)=[O:35])=[CH:30][CH:31]=1)[C:18]1[CH:19]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 810334-Benzyloxyphenylacetic acidHCID 112069772-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-amineHCID 22992078Ethyldimethylpropylcarbodiimide hydrochloride

Product 1

HCID 113166232-(4-phenoxyphenyl)-N-[2-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-pyrrolidin-1-yl-ethyl)-2H-indazol-5-ylamine (56.0 mg, 0.243 mmol), (4-benzyloxy-phenyl)-acetic acid (60.0 mg, 0.248 mmol), ethyldimethypropylcarbodiimide hydrochloride (57.0 mg, 0.298 mmol), N-hydroxybenzotriazole (40.0 mg, 0.296 mmol), N-methylmorpholine (64.0 mg, 0.633 mmol) and 2 mL of N,N-dimethylformamide, were shaken for 6 hours. The solvents were removed under vacuo and the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethylsulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) ppm 1.82(m, 2H), 1.99 (m, 2H), 3.03(m, 2H), 3.52 (m, 2H), 3.64 (s, 2H), 3.80 (m, 2H), 4.78 (t, 2H, J=6.24), 6.97–7.00 (m, 4H), 7.12 (m, 1H), 7.29–7.39 (m, 5H), 7.59 (m, 1H), 8.18 (s, 1H), 8.38 (s, 1H), 10.13 (s, 1H); MS (DCI/NH3) m/z 441 [M+H]+.

Workup

  1. customThe solvents were removed under vacuo
  2. dissolutionthe residue was dissolved in 1.5 mL of a 1:1 mixture of dimethylsulfoxide/methanol
  3. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-43e923fb705549aa84d72f51c101df15
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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