Hydrochloric Acid → (R)-4-(5-(3,4-diethoxybenzyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-amine hydrochloride

HRID 1807608Notes

Reaction equation

HRID 1807608 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:30]=[CH:31][C:32]=1[O:33][CH2:34][CH3:35])[CH2:7][C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][CH2:16][C@H:17]3[NH:22]C(=O)OC(C)(C)C)[N:9]=1)[CH3:2].[ClH:36]>O1CCOCC1>[ClH:36].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:30]=[CH:31][C:32]=1[O:33][CH2:34][CH3:35])[CH2:7][C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][CH2:16][C@H:17]3[NH2:22])[N:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67197789(R)-tert-butyl 4-(5-(3,4-diethoxybenzyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-ylcarbamate

Product 1

HCID 67319265(R)-4-(5-(3,4-diethoxybenzyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-amine hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To (R)-tert-butyl 4-(5-(3,4-diethoxybenzyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-ylcarbamate INT-56 (150 mg, 0.312 mmol) in dioxane (1 mL) was added 4N HCl in dioxane (1 mL). The mixture was stirred at room temperature for 6 h, and product precipitated. The reaction mixture was diluted with Et2O and the solid collected by filtration to produce of (R)-4-(5-(3,4-diethoxybenzyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-amine hydrochloride 65 (125 mg, 96%) as an off-white solid. LCMS-ESI (m/z): calcd for C22H25N3O3: 379.2; found 402.1 [M+Na]+, tR=2.38 min. 1H NMR (400 MHz, DMSO) δ 8.40 (s, 1H), 8.01 (d, J=7.6 Hz, 1H), 7.78 (d, J=7.2 Hz, 1H), 7.53 (t, J=7.7 Hz, 1H), 7.02 (d, J=2.0 Hz, 1H), 6.90 (dt, J=8.2, 5.1 Hz, 2H), 4.81 (s, 1H), 4.35 (s, 2H), 4.01 (p, J=6.9 Hz, 4H), 3.36 (s, 2H), 3.22-3.04 (m, 1H), 2.55-2.43 (m, 2H), 2.05 (dd, J=14.0, 8.4 Hz, 1H), 1.32 (td, J=7.0, 4.0 Hz, 6H).

Workup

  1. customproduct precipitated
  2. additionThe reaction mixture was diluted with Et2O
  3. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-2c4abebbda334a9eadd84c9366343bbf
Source dataset
uspto-grants-2013_01
Patent number
US08357706B2

Reaction notes

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