Hydrochloric Acid → HCID 68999956, compound

HRID 1987975Notes

Reaction equation

HRID 1987975 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-7e52aa0cc38440e1aaa5b908f45c1311
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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