Hydrochloric Acid → HCID 68997312, compound

HRID 1987979Notes

Reaction equation

HRID 1987979 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-5ee2645347f24e59bc78e63c47b53890
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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