Hydrochloric Acid → HCID 68826350, compound

HRID 1355590Notes

Reaction equation

HRID 1355590 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-71b0335c436c471a8322cbbc747ec1ca
Source dataset
uspto-grants-2003_07
Patent number
US06586446B1

Reaction notes

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