Hydrochloric Acid → HCID 68826350, compound

HRID 1987241Notes

Reaction equation

HRID 1987241 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][C@@H:21]3[CH2:23][CH2:24][C@H:18]2[C@H:19]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:20]3)=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[C:33]([C:36]1[CH:37]=[C:38]([NH:42][C:43]([NH:45][CH2:46][CH2:47][CH2:48][N:49]2[CH2:54][C@H:53]3[CH2:55][CH2:56][C@@H:50]2[C@@H:51]([CH2:57][C:58]2[CH:63]=[CH:62][C:61]([F:64])=[CH:60][CH:59]=2)[CH2:52]3)=[O:44])[CH:39]=[CH:40][CH:41]=1)(=[O:35])[CH3:34].[ClH:65].C(OCC)C>ClCCl>[ClH:65].[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][C@@H:21]3[CH2:23][CH2:24][C@H:18]2[C@H:19]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[CH2:20]3)=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[ClH:65].[C:33]([C:36]1[CH:37]=[C:38]([NH:42][C:43]([NH:45][CH2:46][CH2:47][CH2:48][N:49]2[CH2:54][C@H:53]3[CH2:55][CH2:56][C@@H:50]2[C@@H:51]([CH2:57][C:58]2[CH:59]=[CH:60][C:61]([F:64])=[CH:62][CH:63]=2)[CH2:52]3)=[O:44])[CH:39]=[CH:40][CH:41]=1)(=[O:35])[CH3:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68826351HCID 68826351, compoundHCID 68826951HCID 68826951, compound

Product 2

HCID 68826350HCID 68826350, compoundYield 100%HCID 68827804HCID 68827804, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-acetylphenyl)-N′-[3-[(1S,4R,6S)-6-[(4-fluorophenyl)methyl]-2-azabicyclo[2.2.2]oct-2-yl]propyl]urea and N-(3-acetylphenyl)-N′-[3-[(1R,4S,6R)-6-[(4-fluorophenyl)methyl]-2-azabicyclo[2.2.2]oct-2-yl]propyl]urea (8.5 mg, 0.019 mmol) in dichloromethane (10 mL) was added 1N hydrogen chloride in diethyl ether (21 μL, 0.021 mmol). The resulting suspension was stirred for 10 min and was then concentrated. The residue was dissolved in acetonitrile (1 mL) and water (7 mL) and lyopholized to afford N-(3-acetylphenyl)-N′-[3-[(1S,4R,6S)-6-[(4-fluorophenyl)methyl]-2-azabicyclo[2.2.2]oct-2-yl]propyl]urea hydrochloride and N-(3-acetylphenyl)-N′-[3-[(1R,4S,6R)-6-[(4-fluorophenyl)methyl]-2-azabicyclo[2.2.2]oct-2-yl]propyl]urea hydrochloride (9.0 mg, 100%) as an amorphous solid. MS (ESI) 438 (M-Cl).

Workup

  1. concentrationwas then concentrated
  2. dissolutionThe residue was dissolved in acetonitrile (1 mL)

Sources & evidence

ORD record
ord-bf24a9c4383b4fb3ad908cd5b27bc748
Source dataset
uspto-grants-2009_06
Patent number
US07550500B2

Reaction notes

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