Hydrochloric Acid → HCID 68998426, compound

HRID 2059683Notes

Reaction equation

HRID 2059683 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][CH:22]4[CH2:24][CH2:23]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]([CH2:21][CH:22]4[CH2:24][CH2:23]4)=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68996694HCID 68996694, compound

Product 1

HCID 68998426HCID 68998426, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (S)—N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(cyclopropylmethyl)benzoxazole-4-carboxamide (94 mg, 0.29 mmol) in methanol (0.5 mL) was added a solution of HCl in diethyl ether (1 N, 0.32 mL, 0.34 mmol) at 0° C. 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-(cyclopropylmethyl)benzoxazole-4-carboxamide hydrochloride (81 mg, 77%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.12 (br s, 1H), 9.36 (d, J=6.6 Hz, 1H), 7.97 (d, J=8.1 Hz, 2H), 7.46 (t, J=7.9 Hz, 1H), 4.45-4.38 (m, 1H), 3.80-3.47 (m, 1H), 3.28-3.22 (m, 2H), 3.15 (dd, J=14.0, 4.5 Hz, 1H), 3.00 (d, J=7.0 Hz, 2H), 2.30-2.16 (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-39023368a46948d7b02af49f30ba1371
Source dataset
uspto-grants-2012_10
Patent number
US08278301B2

Reaction notes

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