Hydrochloric Acid → (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(1-methylcyclopropyl)benzoxazole-4-carboxamide hydrochloride

HRID 2059679Notes

Reaction equation

HRID 2059679 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([CH3:24])[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]([C:21]4([CH3:24])[CH2:23][CH2:22]4)=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68995673(S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(1-methylcyclopropyl)benzoxazole-4-carboxamide

Product 1

HCID 68995672(S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(1-methylcyclopropyl)benzoxazole-4-carboxamide hydrochlorideYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (S)—N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(1-methylcyclopropyl)benzoxazole-4-carboxamide (63 mg, 0.19 mmol) in methanol (2 mL) was added a solution of HCl in diethyl ether (1 N, 0.38 mL, 0.38 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-(1-methylcyclopropyl)benzoxazole-4-carboxamide hydrochloride (60 mg, 88%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.22 (br s, 1H), 9.36 (d, J=6.6 Hz, 1H), 8.10 (d, J=8.0 Hz, 2H), 7.46 (t, J=7.9 Hz, 1H), 4.45-4.36 (m, 1H), 3.77-3.70 (m, 1H), 3.35-3.26 (m, 2H), 3.24 (t, J=7.9 Hz, 2H), 3.17 (dd, J=13.2, 3.7 Hz, 1H), 2.30-2.15 (m, 2H), 2.00-1.90 (m, 3H), 1.61 (s, 3H), 1.48-1.40 (m, 2H), 1.20-1.15 (m, 2H); MS (ESI+) m/z 326 (M+H); HPLC >99% (AUC), tR=11.65 min.

Workup

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

Sources & evidence

ORD record
ord-1f9914b4ce534bffa5a28806f21a58ad
Source dataset
uspto-grants-2012_10
Patent number
US08278301B2

Reaction notes

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