4-Methylmorpholine → HCID 22036601, compound

HRID 1790145Notes

Reaction equation

HRID 1790145 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[CH2:7][NH:6]1.[O:17]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](O)=[O:32])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.Cl.C(N=C=NC(C)(C)CC)C>CN(C=O)C.O.C(OCC)C>[CH3:16][O:15][CH:3]([O:2][CH3:1])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:31](=[O:32])[CH2:30][C:27]3[CH:28]=[CH:29][C:24]([O:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:25][CH:26]=3)[CH:12]=2)[CH:7]=[N:6]1

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2390774-Phenoxyphenylacetic acidHCID 22992078Ethyldimethylpropylcarbodiimide hydrochlorideHCID 69652717HCID 69652717, compound

Product 1

HCID 22036601HCID 22036601, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2,2-dimethoxyethyl)-2H-indazol-6-ylamine (1.89 g, 8.60 mmol), 4-phenoxyphenylacetic acid (2.06 g, 9.03 mmol), N-methyl morpholine (2.26 mL, 20.6 mmol), HOBt (1.45 g, 10.75 mmol), and ethyldimethylpropylcarbodiimide hydrochloride (2.06 g, 10.75 mmol) in DMF (40 mL) was stirred at room temperature for 3 hours, diluted with H2O (40 mL) and diethyl ether (30 mL). The layers were separated, and the aqueous was extracted with additional diethyl ether (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to provide a yellow oil which was purified by MPLC (SiO2, 1:1 hexane:ethyl acetate to 1:3 hexane:ethyl acetate) to provide N-[1-(2,2-dimethoxyethyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide as a yellow solid. 1H NMR (300 MHz, DMSO-D6) δ ppm 3.26 (m, 6 H), 3.68 (s, 2 H), 4.37 (d, J=5.42 Hz, 2 H), 4.73 (t, J=5.42 Hz, 1 H), 6.98 (m, 4 H), 7.15 (m, 2 H), 7.38 (m, 4 H), 7.66 (m, 1 H), 7.97 (m, 1 H), 8.11 (s, 1 H), and 10.35 (s, 1 H); MS (ESI) 431 (M−H)−.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with additional diethyl ether (3×50 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto provide a yellow oil which
  7. customwas purified by MPLC (SiO2, 1:1 hexane:ethyl acetate to 1:3 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-617281cfdb2a4aca86b9036de7f9c7ef
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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