Ethyl bromoacetate → HCID 67335596, compound

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

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.