Water → HCID 54597001, compound

HRID 85456Notes

Reaction equation

HRID 85456 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=O)[C:5]2[CH:6]=[N:7][N:8]([CH2:11][CH3:12])[C:9]=2[CH:10]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C.[NH2:48][CH2:49][C:50]1[C:51](=[O:60])[NH:52][C:53]([CH3:59])=[CH:54][C:55]=1[CH2:56][CH2:57][CH3:58]>C(Cl)Cl>[CH3:59][C:53]1[NH:52][C:51](=[O:60])[C:50]([CH2:49][NH:48][C:13]([C:4]2[C:5]3[CH:6]=[N:7][N:8]([CH2:11][CH3:12])[C:9]=3[CH:10]=[C:2]([Br:1])[CH:3]=2)=[O:15])=[C:55]([CH2:56][CH2:57][CH3:58])[CH:54]=1

Participants

8

Reactant 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateHCID 674648836-bromo-1-ethyl-1H-indazole-4-carboxylic acid

Product 1

HCID 54597001HCID 54597001, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 6-bromo-1-ethyl-1H-indazole-4-carboxylic acid, 4 (450 mg, 1.67 mmol) in DCM (50 mL) were added EDC.HCl (384 mg, 2.00 mmol), HOBt.H2O (306 mg, 2.00 mmol) and then stirred for 15 min at RT. To the resulting mixture, DIPEA (1.2 mL, 5.59 mmol) followed by 3-aminomethyl-6-methyl-4-propyl-1H-pyridin-2-one (301 mg, 1.67 mmol) were added and the contents stirred for 18 h at RT. The reaction mixture was diluted with DCM (50 mL) and washed with water (2×50 mL), 10% aq citric acid solution (2×50 mL), saturated aq NaHCO3 solution (2×30 mL) and brine (2×50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained solid was washed with diethyl ether (2×50 mL) to afford the title compound as a white solid (230 mg, 32%). 1H NMR (400 MHz, DMSO-d6): δ 0.83-0.79 δ (t, 3H), 1.38 (t, 3H), 1.55 (m, 2H), 2.15 (s, 3H), 2.49 (s, 2H), 4.38 (d, 2H), 4.43 (m, 2H), 5.90 (s, 1H), 7.64 (d, 1H), 8.19 (s, 1H), 8.38 (s, 1H), 8.61 (m, 1H), 11.51 (bs, 1H). LCMS (ES+): m/z=431.15.

Workup

  1. additionwere added
  2. washwashed with water (2×50 mL), 10% aq citric acid solution (2×50 mL), saturated aq NaHCO3 solution (2×30 mL) and brine (2×50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washThe obtained solid was washed with diethyl ether (2×50 mL)

Sources & evidence

ORD record
ord-42b017f8667b4c0bb5e1b8cbcb15787c
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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