4-Methylmorpholine → HCID 11246988, compound

HRID 1825828Notes

Reaction equation

HRID 1825828 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([NH2:14])=[CH:11]2)=[N:6]1.[O:16]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([NH:14][C:30](=[O:31])[CH2:29][C:26]3[CH:27]=[CH:28][C:23]([O:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:24][CH:25]=3)=[CH:11]2)=[N:6]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2390774-Phenoxyphenylacetic acidHCID 22138917HCID 22138917, compound

Product 1

HCID 11246988HCID 11246988, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-Dimethylamino-ethyl)-2H-indazol-5-ylamine (49.0 mg, 0.243 mmol), (4-phenoxy-phenyl)-acetic acid (60.0 mg, 0.248 mmol), EDCI (57.0 mg, 0.298 mmol), N-hydroxybenzotriazole (40.0 mg, 0.296 mmol), N-methyl morpholine (64.0 mg, 0.633 mmol) and 2 mL of N,N-dimethylformamide was shaken for 6 hours. The solvents were removed under vacuo and the residue dissolved in 1.5 mL of a 1:1 mixture of dimethylsulfoxide/methanol was purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) ppm 2.49(s, 6H) 3.34 (t, 2H, J=6.44), 3.37 (s, 2H), 4.50 (t, 2H, J=6.44), 6.69–6.74 (m, 4H), 6.85 (m, 1H), 7.03 (m, 1H), 7.08–7.13 (m, 4H), 7.32 (m, 1H), 7.90 (s, 1H), 8.10 (s, 1H), 9.26 (s, 1H); MS (DCI/NH3) m/z 415 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-c6fedad85cfa4f268c89e66b7f3258de
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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