Hydrochloric Acid → HCID 68995728, compound

HRID 1987977Notes

Reaction equation

HRID 1987977 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-dea03bd2918a4775b4fe6b2f21a95abf
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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