Hydrochloric Acid → HCID 178511229, compound

HRID 449081Notes

Reaction equation

HRID 449081 reaction equation
C(OC(=O)[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:26]3[C:21]([C:22]([NH2:27])=[N:23][CH:24]=[N:25]3)=[C:20]([C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:30][CH:29]=3)[N:19]=2)[CH2:14][CH2:13]1)C1C=CC=CC=1.Cl>O1CCOCC1>[NH2:10][CH2:11][C@H:12]1[CH2:13][CH2:14][C@H:15]([C:18]2[N:26]3[C:21]([C:22]([NH2:27])=[N:23][CH:24]=[N:25]3)=[C:20]([C:28]3[CH:29]=[CH:30][C:31]([O:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[CH:32][CH:33]=3)[N:19]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178508823HCID 178508823, compound

Product 1

HCID 178511229HCID 178511229, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of trans-{4-[4-amino-5-(4-phenoxy-phenyl)-imidazo[5,1-f][1,2,4]triazin-7-yl]-cyclohexylmethyl}-carbamic acid benzyl ester (20.0 mg, 0.0364 mmol) and 4 M of HCl in 1,4-dioxane (2 mL) was heated to reflux overnight. The solution was concentrated in vacuo and left to dry in the vacuum oven overnight to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=1.23-1.37 (m, 2H), 1.83-1.99 (m, 3H), 2.03-2.09 (m, 2H), 2.15-2.24 (m, 2H), 2.86 (d, J=4.0 Hz, 2H), 3.44-3.56 (m, 1H), 7.12 (d, J=8.1 Hz, 2H), 7.17-7.26 (m, 3H), 7.44 (t, J=7.8 Hz, 3H), 7.66 (d, J=3.5 Hz, 2H), 8.00-8.10 (m, 1H). MS (ES+): m/z 415.02 (100) [MH+]. HPLC: tR=2.26 min (OpenLynx, polar—5 min).

Workup

  1. temperatureto reflux overnight
  2. concentrationThe solution was concentrated in vacuo
  3. waitleft
  4. customto dry in the vacuum oven overnight

Sources & evidence

ORD record
ord-a3888b8a5e094e2f8658f7c4b0111f76
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…