4-Methylmorpholine → N-[1-(3,3-dimethoxypropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide

HRID 1790148Notes

Reaction equation

HRID 1790148 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[CH:8]=[N:7]1.[O:18]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.Cl.C(N=C=NC(C)(C)CC)C>CN(C=O)C.C(OCC)C.O>[CH3:17][O:16][CH:3]([O:2][CH3:1])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][C:32](=[O:33])[CH2:31][C:28]3[CH:29]=[CH:30][C:25]([O:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:26][CH:27]=3)[CH:13]=2)[CH:8]=[N:7]1

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2390774-Phenoxyphenylacetic acidHCID 22992078Ethyldimethylpropylcarbodiimide hydrochlorideHCID 696527361h-Indazol-6-amine,1-(3,3-dimethoxypropyl)-

Product 1

HCID 22036559N-[1-(3,3-dimethoxypropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3,3-dimethoxypropyl)-1H-indazole-6-ylamine (1.32 g, 5.60 mmol), 4-phenoxyphenylacetic acid (1.34 g, 5.88 mmol), N-methyl morpholine (1.47 mL, 13.4 mmol), HOBt (945 mg, 7.0 mmol), and ethyldimethylpropylcarbodiimide hydrochloride (1.34 g, 7.0 mmol) in DMF (28 mL) was stirred at room temperature for 3 hours followed by the addition of H2O (40 mL) and diethyl ether (30 mL). The layers were separated, and the aqueous was extracted with diethyl ether (3×30 mL). The combined organic layers were dried (Na2SO4), filtered, concentrated under reduced pressure and purified by MPLC (SiO2, 1:1 hexane:ethyl acetate to 1:3 hexane:ethyl acetate) to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 2.05 (m, 2 H), 3.22 (m, 6 H), 3.68 (s, 2 H), 4.29 (m, 3 H), 6.99 (m, 4 H), 7.14 (m, 2 H), 7.38 (m, 4 H), 7.66 (m, 1 H), 7.97 (s, 1 H), 8.12 (s, 1 H), and 10.34 (s, 1 H); MS (ESI) 444 (M−H)−.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with diethyl ether (3×30 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified by MPLC (SiO2, 1:1 hexane:ethyl acetate to 1:3 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-f933d4246fc24498b2d7e5d7f99e055d
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

Loading…