Hydrochloric Acid → HCID 68455869, compound

HRID 969914Notes

Reaction equation

HRID 969914 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[S:25][CH:24]=[N:23][C:22]=4[CH3:26])=[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]([C:21]4[S:25][CH:24]=[N:23][C:22]=4[CH3:26])=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68455870HCID 68455870, compound

Product 1

HCID 68455869HCID 68455869, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(4-methylthiazol-5-yl)benzoxazole-4-carboxamide (45 mg, 0.12 mmol) in methanol (2.0 mL) was added a solution of HCl in diethyl ether (1 N, 1.5 mL, 1.5 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-(4-methylthiazol-5-yl)benzoxazole-4-carboxamide hydrochloride (40 mg, 74%) as a light yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 10.46 (s, 1H), 9.35 (s, 1H), 9.10 (d, J=6.3 Hz, 1H), 8.05 (dd, J=8.2, 0.9 Hz, 1H), 7.94 (dd, J=7.7, 0.9 Hz, 1H), 7.58 (t, J=8.0 Hz, 1H), 4.44-4.40 (m, 1H), 3.64-3.55 (m, 1H), 3.35-3.15 (m, 5H), 2.91(s, 3H), 2.33-2.25 (m, 2H), 2.00-1.95 (m, 3H); MS (ESI+) m/z 369 (M+H); HPLC>99% (AUC), tR=12.05 min.

Workup

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

Sources & evidence

ORD record
ord-a9fbdba9e3964d759b91f2bff66d16fd
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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