Hydrochloric Acid → HCID 68997312, compound

HRID 2059689Notes

Reaction equation

HRID 2059689 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[CH2:24][CH2:23][CH2:22]4)=[N:18][C:17]=13)=[O:11])[CH2:2]2.[ClH:25]>CO.C(OCC)C>[ClH:25].[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]4)=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68997313HCID 68997313, compound

Product 1

HCID 68997312HCID 68997312, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (S)—N-(1-azabicyclo[2.2.2]oct-3-yl)-2-cyclobutylbenzoxazole-4-carboxamide (226 mg, 0.69 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-cyclobutylbenzoxazole-4-carboxamide hydrochloride (151 mg, 60%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 12.68 (br s, 1H), 9.61 (d, J=7.0 Hz, 1H), 8.13 (dd, J=7.8, 1.0 Hz, 1H), 7.62 (dd, J=8.0, 0.9 Hz, 1H), 7.44 (t, J=7.8 Hz, 1H), 4.68-4.62 (m, 1H), 3.90-3.75 (m, 2H), 3.50-3.23 (m, 5H), 2.60-2.50 (m, 5H), 2.40-2.30 (m, 1H), 2.25-1.95 (m, 5H); MS (ESI+) m/z 326 (M+H); HPLC >99% (AUC), tR=11.60 min.

Workup

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

Sources & evidence

ORD record
ord-9865602e54544ffd873abd36cbad4019
Source dataset
uspto-grants-2012_10
Patent number
US08278301B2

Reaction notes

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