Ethyl bromoacetate → HCID 67335596, compound

HRID 1672158Notes

Reaction equation

HRID 1672158 reaction equation
[NH2:1][CH2:2][C:3]1([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[CH:13]3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20].CCN(CC)CC>C1COCC1>[CH2:19]([O:21][C:22](=[O:25])[CH2:23][NH:1][CH2:2][C:3]1([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[CH:13]3)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1)[CH3:20]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 67335147HCID 67335147, compound

Product 1

HCID 67335596HCID 67335596, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (1-aminomethyl-cyclohexyl)-(1H-indazol-5-yl)-amine (0.775 g, 3.18 mmol) in THF (7 mL) at 0° C. under nitrogen was added ethylbromoacetate (0.530 g, 0.351 mL, 3.18 mmol) and Et3N (1.42 mL, 10.2 mmol) then the reaction mixture warmed to room temperature. After 90 minutes the mixture was concentrated in vacuo then redissolved in DCM (100 mL) and washed with saturated aqueous NaHCO3 and brine, then dried (MgSO4), filtered and concentrated in vacuo to an oil (1.4 g). Purification by chromatography (silica, 0 to 10% of a 9:1 MeOH:NH4OH solution in DCM) gave {[1-(1H-indazol-5-ylamino)-cyclohexylmethyl]-amino}-acetic acid ethyl ester (0.877 g, 2.66 mmol, 84%) as a solid.

Workup

  1. concentrationAfter 90 minutes the mixture was concentrated in vacuo
  2. dissolutionthen redissolved in DCM (100 mL)
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to an oil (1.4 g)
  7. customPurification by chromatography (silica, 0 to 10% of a 9:1 MeOH:NH4OH solution in DCM)

Sources & evidence

ORD record
ord-419f376c2bbd41908b6191ca8515e3cf
Source dataset
uspto-grants-2011_08
Patent number
US07998963B2

Reaction notes

Loading…