Potassium Carbonate → N-(2-{7-[(2S)-3-(4-Cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl}ethyl)-1-phenylmethanesulfonamide

HRID 1992398Notes

Reaction equation

HRID 1992398 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:11][CH:10]2[O:12][CH:6]([CH2:7][N:8]([CH2:13][C@H:14]([OH:25])[CH2:15][O:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[CH2:9]2)[CH2:5]1.[C:26]1([CH2:32][S:33](Cl)(=[O:35])=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(N(CC)CC)C.C(#N)C>[C:21]([C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][C@@H:14]([OH:25])[CH2:13][N:8]2[CH2:9][CH:10]3[O:12][CH:6]([CH2:5][N:4]([CH2:3][CH2:2][NH:1][S:33]([CH2:32][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:35])=[O:34])[CH2:11]3)[CH2:7]2)=[CH:24][CH:23]=1)#[N:22]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 74740Phenylmethanesulfonyl chlorideHCID 685227854-{(2S)-3-[7-(2-Aminoethyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-2-hydroxypropoxy}benzonitrile

Product 1

HCID 11677749N-(2-{7-[(2S)-3-(4-Cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl}ethyl)-1-phenylmethanesulfonamideYield 72%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

4-{(2S)-3-[7-(2-Aminoethyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-2-hydroxypropoxy}benzonitrile (0.096 g, 0.28 mmol; see step Preparation A above) was dissolved in a 1:2 ratio of DCM:acetonitrile (3 mL). Triethylamine (0.17 g, 1.68 mmol) was added, followed by phenylmethanesulfonyl chloride (0.068 g, 0.36 mmol). The mixture was stirred at room temperature overnight with K2CO3 (0.38 g, 2.77 mmol) to ensure that the free base of triethylamine was in the reaction mixture. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. Purification by preparative HPLC gave 0.1 g (72%) of the title compound.

Workup

  1. customstep Preparation A above)
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-3d2dee7074094c1bae4eecfbea76a7fc
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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