Hydrochloric Acid → HCID 68999956, compound

HRID 2059685Notes

Reaction equation

HRID 2059685 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]3[O:20][C:19]([C@H:21]4[CH2:23][CH:22]4[CH3:24])=[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)[CH:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]3[O:20][C:19]([C@H:21]4[CH2:23][CH:22]4[CH3:24])=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68998082HCID 68998082, compound

Product 1

HCID 68999956HCID 68999956, compoundYield 51%

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-methylcyclopropyl)benzoxazole-4-carboxamide (149 mg, 0.45 mmol) in methanol (0.5 mL) was added a solution of HCl in diethyl ether (1 N, 0.92 mL, 0.92 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-methylcyclopropyl)benzoxazole-4-carboxamide hydrochloride (82 mg, 51%) as a white solid and as a mixture of diastereomers: 1H NMR (500 MHz, DMSO-d6) δ 12.68 (br s, 1H), 9.51 (br s, 1H), 8.12 (d, J=8.0 Hz, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.38 (t, J=7.9 Hz, 1H), 4.69-4.58 (m, 1H), 3.80-3.70 (m, 1H), 3.50-3.20 (m, 5H), 2.60-2.50 (m, 1H), 2.40-2.35 (m, 1H), 2.25-1.95 (m, 4H), 1.65-1.60 (m, 1H), 1.50-1.42 (m, 1H), 1.35-1.30 (m, 2H), 1.17-1.10 (m, 2H); MS (ESI+) m/z 326 (M+H); HPLC 98.9% (AUC), tR=11.59 min.

Workup

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

Sources & evidence

ORD record
ord-c3cf78811e484720a98a332600938fe2
Source dataset
uspto-grants-2012_10
Patent number
US08278301B2

Reaction notes

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