Dichloromethane → HCID 131731428, compound

HRID 400774Notes

Reaction equation

HRID 400774 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)[N:15]=2)=[CH:10][C:9]=1[C:36]([F:39])([F:38])[F:37].C(Cl)[Cl:41]>C(O)(C(F)(F)F)=O>[ClH:41].[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[CH2:25][NH:24][CH2:23][CH2:22]4)[N:15]=2)=[CH:10][C:9]=1[C:36]([F:39])([F:37])[F:38]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 67399198HCID 67399198, compound

Product 1

HCID 131731428HCID 131731428, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl 6-{5-[4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-3,4-dihydroisoquinoline-2(1H)-carboxylate obtained from step 1 was dissolved in DCM (3 mL) and TFA (1 mL). The resulting solution was stirred at RT for 1 hour and the solvent was evaporated in vacuo to give a light yellow oil. The latter was filtered through a short plug of alumina (c-hexane/EtOAc, 80/20 then 50/50) to give a light yellow oil that was triturated in a Et2O/HCl (1 M) mixture (1:1, 2 mL), filtered and washed with Et2O to the title compound as an off-white solid. 1H NMR (DMSO-d6) δ 9.30 (bs, 2H), 8.45-8.41 (m, 1H), 8.38 (m, 1H), 8.01-7.98 (m, 2H), 7.86 (d, J=8.5 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 4.41 (m, 2H), 3.54-3.42 (m, 3H), 3.18-3.08 (m, 3H), 2.97-2.93 (m, 1H), 2.65-2.59 (m, 1H), 1.80-1.77 (m, 2H), 1.63-1.30 (m, 4H), 0.78 (d, J=6 Hz, 3H). HPLC (Method A) Rt 4.61 min (Purity: 100.0%). LC/MS (method B): 443.2 (M+H)+.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customto give a light yellow oil
  3. filtrationThe latter was filtered through a short plug of alumina (c-hexane/EtOAc, 80/20
  4. custom50/50) to give a light yellow oil that
  5. customwas triturated in a Et2O/HCl (1 M) mixture (1:1, 2 mL)
  6. filtrationfiltered
  7. washwashed with Et2O to the title compound as an off-white solid

Sources & evidence

ORD record
ord-792c42affd0542d6be5b613229801c64
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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