Dabco → N-(pyrimidin-4-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide

HRID 1696123Notes

Reaction equation

HRID 1696123 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[NH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][N:25]=1.C1N2CCN(CC2)C1>C(#N)C>[N:27]1[CH:28]=[CH:29][C:24]([NH:23][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH:8]3[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C:2]([F:22])([F:21])[F:1])[CH2:6][CH2:7]3)=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[N:25][CH:26]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 689584-AminopyrimidineHCID 179734784-(1-(2,2,2-Trifluoroacetyl)piperidin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 59465873N-(pyrimidin-4-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamideYield 36.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

Prepared using general procedure 15, method B. Prepared using a mixture of 4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzene-1-sulfonyl chloride (2.0 g, 5.6 mmol), 4-aminopyrimidine (535 mg, 5.6 mmol), DABCO (3.1 g, 28.0 mmol) and acetonitrile (10 mL). The reaction mixture was heated at 40° C. for 6 h. Purification via silica gel chromatography using 5% MeOH in CH2Cl2 gave N-(pyrimidin-4-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide (850 mg, 36%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=415.3; tR=2.57 min.

Workup

  1. customPrepared
  2. customPrepared
  3. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-5bcf952db2b642029ee57ef54df2cda6
Source dataset
uspto-grants-2012_04
Patent number
US08163720B2

Reaction notes

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