Hydrochloric Acid → (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide Hydrochloride

HRID 969853Notes

Reaction equation

HRID 969853 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]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[OH:27])=[N:18][C:17]=13)=[O:11])[CH2:2]2.[ClH:28]>CO.C(OCC)C>[ClH:28].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@H:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]3[O:20][C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[OH:27])=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136344232(S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide

Product 1

HCID 136344231(S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide HydrochlorideYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide (46 mg, 0.12 mmol) in methanol (1.0 mL) was added a solution of HCl in diethyl ether (1 N, 0.13 mL, 0.13 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-(2-hydroxyphenyl)benzoxazole-4-carboxamide hydrochloride (36 mg, 72%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.93 (s, 1H), 10.07 (br s, 1H), 9.29 (d, J=6.5 Hz, 1H), 8.08 (dd, J=7.8, 1.6 Hz, 1H), 8.03 (dd, J=8.1, 0.9 Hz, 1H), 7.90 (dd, J=7.7, 0.8 Hz, 1H), 7.59-7.51 (m, 2H), 7.19 (d, J=8.3 Hz, 1H), 7.12-7.06 (m, 1H), 4.50-4.42 (m, 1H), 3.80-3.70 (m, 1H), 3.40-3.20 (m, 5H), 2.35-2.25 (m, 2H), 2.00-1.95 (m, 2H), 1.95-1.85 (m, 1H); MS (ESI+) m/z 364 (M+H); HPLC>99% (AUC), tR=11.64 min.

Workup

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

Sources & evidence

ORD record
ord-65af08ed1eaa4954b881cbe8b2e849e9
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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