Hydrochloric Acid → HCID 68995728, compound

HRID 2059687Notes

Reaction equation

HRID 2059687 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]3[O:20][C:19]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:18][C:17]=13)=[O:11])[CH2:2]2.[ClH:27]>CO.C(OCC)C>[ClH:27].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]3[O:20][C:19]([CH:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68995729HCID 68995729, compound

Product 1

HCID 68995728HCID 68995728, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (S)—N-(1-azabicyclo[2.2.2]oct-3-yl)-2-cyclohexylbenzoxazole-4-carboxamide (136 mg, 0.39 mmol) in methanol (1.0 mL) was added a solution of HCl in diethyl ether (1 N, 0.8 mL, 0.8 mmol) at room temperature slowly. The reaction mixture was diluted with diethyl ether. The resulting solid was filtered and washed with diethyl ether to afford (S)—N-(1-azabicyclo[2.2.2]oct-3-yl)-2-cyclohexylbenzoxazole-4-carboxamide hydrochloride (147 mg, 96%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 12.68 (br s, 1H), 9.62 (d, J=6.5 Hz, 1H), 8.11 (dd, J=7.8, 1.0 Hz, 1H), 7.67 (dd, J=8.0, 0.9 Hz, 1H), 7.43 (t, J=7.9 Hz, 1H), 4.70-4.63 (m, 1H), 3.80-3.74 (m, 1H), 3.45-3.28 (m, 3H), 3.25-3.15 (m, 1H), 3.07-3.00 (m, 1H), 2.53-2.46 (m, 1H), 2.40-2.30 (m, 1H), 2.24-2.07 (m, 4H), 2.05-1.95 (m, 1H), 1.93-1.84 (m, 2H), 1.83-1.63 (m, 4H), 1.55-1.42 (m, 2H), 1.40-1.30 (m, 1H); MS (ESI+) m/z 354 (M+H); HPLC >99% (AUC), tR=12.30 min.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1c4cb8855f414cb0a8327e2bafed92fa
Source dataset
uspto-grants-2012_10
Patent number
US08278301B2

Reaction notes

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