Hydrochloric Acid → HCID 69001040, compound

HRID 2059681Notes

Reaction equation

HRID 2059681 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]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:18][C:17]=13)=[O:11])[CH2:2]2.[ClH:28]>CO.C(OCC)C>[ClH:28].[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]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68999163HCID 68999163, compound

Product 1

HCID 69001040HCID 69001040, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (S)—N-(1-azabicyclo[2.2.2]oct-3-yl)-2-benzylbenzoxazole-4-carboxamide (84 mg, 0.23 mmol) in methanol (1.5 mL) was added a solution of HCl in diethyl ether (1 N, 0.5 mL, 0.5 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-benzylbenzoxazole-4-carboxamide hydrochloride (71 mg, 78%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.05 (br s, 1H), 9.19 (d, J=7.1 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.88 (d, J=8.0 Hz, 1H), 7.52 (t, J=7.9 Hz, 1H), 7.45-7.30 (m, 5H), 4.48 (s, 2H), 4.37-4.32 (m, 1H), 3.75-3.65 (m, 1H), 3.22-3.15 (m, 3H), 3.10-3.05 (m, 2H), 2.15-2.10 (m, 1H), 1.95-1.90 (m, 2H), 1.80-1.60 (m, 2H); MS (ESI+) m/z 362 (M+H); HPLC >99% (AUC), tR=11.81 min.

Workup

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

Sources & evidence

ORD record
ord-5094d733621c4dc39616ea3705725fe7
Source dataset
uspto-grants-2012_10
Patent number
US08278301B2

Reaction notes

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