Diisopropylethylamine → 4-Fluoro-2-[4-(5-methanesulfonyl-2-pyrrolidin-1-yl-benzoyl)-piperazin-1-yl]-benzonitrile

HRID 32692Notes

Reaction equation

HRID 32692 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:9]([CH:13]=1)[C:10]([OH:12])=O)(=[O:4])=[O:3].[F:19][C:20]1[CH:27]=[C:26]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:24][C:21]=1C#N.[CH3:34][N:35](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(O)=O>[F:19][C:20]1[CH:21]=[CH:24][C:25]([C:34]#[N:35])=[C:26]([N:28]2[CH2:29][CH2:30][N:31]([C:10](=[O:12])[C:9]3[CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=3[N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:32][CH2:33]2)[CH:27]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 187600452-Fluoro-4-(piperazin-1-YL)benzonitrileHCID 597934895-Methanesulfonyl-2-pyrrolidin-1-yl-benzoic acid

Product 1

HCID 688398384-Fluoro-2-[4-(5-methanesulfonyl-2-pyrrolidin-1-yl-benzoyl)-piperazin-1-yl]-benzonitrile

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 13.6 mg (0.05 mmol) 5-Methanesulfonyl-2-pyrrolidin-1-yl-benzoic acid, 15.7 mg (0.06 mmol) 2-Fluoro-4-piperazin-1-yl-benzonitrile (Org. Proc. Res. Dev. 1999, 460), 17.9 mg (0.06 mmol) TBTU and 43 ul (0.25 mmol) DIPEA in 1 ml DMF was stirred for 16 h at room temperature. After addition of 100 ul formic acid the mixture was subjected to preparative HPLC purification on reversed phase eluting with an acetonitrile/water gradient to yield after evaporation of the product fractions 10.6 mg (33%) of the title compound. MS (m/e): 457.2 (MH+, 100%)

Workup

  1. customwas subjected to preparative HPLC purification on reversed phase
  2. washeluting with an acetonitrile/water gradient
  3. customto yield
  4. customafter evaporation of the product fractions 10.6 mg (33%) of the title compound

Sources & evidence

ORD record
ord-20e4e46796454313b8db48858a80962e
Source dataset
uspto-grants-2008_09
Patent number
US07427612B2

Reaction notes

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