Hydrochloric Acid → HCID 131731429, compound

HRID 400775Notes

Reaction equation

HRID 400775 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:24]=[C:23]4[C:18]([CH2:19][CH2:20][N:21]([CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])[CH2:22]4)=[CH:17][CH:16]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39].[ClH:40]>O1CCOCC1>[ClH:40].[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:24]=[C:23]4[C:18]([CH2:19][CH2:20][N:21]([CH2:25][C:26]([OH:28])=[O:27])[CH2:22]4)=[CH:17][CH:16]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123454999HCID 123454999, compound

Product 1

HCID 131731429HCID 131731429, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-butyl [7-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-3,4-dihydroisoquinolin-2(1H)-yl]acetate obtained from step 1 was dissolved in HCl in dioxane (4M, 10 mL), stirred at rt for 30 hours. Solvents were removed under vacuum, Et2O added and the solid residue filtered after which solid was triturated in hot CH3CN and filtered to give the title compound as a light green powder. 1H NMR (DMSO-d6) δ 8.32 (m, 1H), 8.17-8.15 (m, 1H), 8.04-8 (m, 2H), 7.49 (d, J=8.1 Hz, 1H), 7.42 (d, J=7.8 Hz, 1H), 7.36-7.27 (m, 3H), 7.15-7.13 (m, 1H), 4.60 (bs, 2H), 4.24-4.13 (m, 4H), 3.60 (bs, 2H), 3.25-3.22 (m, 5H), 2.03 (s, 3H). HPLC (Method A) Rt 4.47 min (Purity: 93.4%). LC/MS (method B): 470.3 (M+H)+.

Workup

  1. customSolvents were removed under vacuum, Et2O
  2. additionadded
  3. filtrationthe solid residue filtered after which solid
  4. customwas triturated in hot CH3CN
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c5a07fc894214428842404148ba8d4e0
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

Loading…