Pyridine → HCID 46180827, compound

HRID 2380962Notes

Reaction equation

HRID 2380962 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N1C=CC=CC=1.C(O)C(N)(CO)CO>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)=[O:15])=[CH:12][CH:13]=2)[S:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:38])=[O:37])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 7369Benzenesulfonyl chlorideHCID 67130576HCID 67130576, compound

Product 1

HCID 46180827HCID 46180827, compoundYield 125.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(4-chloro-benzylamino)-phenyl]-(4-phenyl-piperazin-1-yl)-methanone (30 mg, 0.07 mmol) and phenylsulfonyl chloride (14.2 μl, 0.11 mmol) in anhydrous dichloromethane (1 ml) was added pyridine (7.2 μl, 0.09 mmol) and the reaction was stirred at ambient for 18 hours. PS-trisamine (32 mg, 0.13 mmol) was added and the mixture was agitated for 3 hours then filtered. The filtrate was concentrated in vacuo to afford the title compound as a yellow solid (48 mg, 98% yield). HPLC retention time 7.7 min. Mass spectrum (ES+) m/z 547 (M+H).

Workup

  1. stirringthe mixture was agitated for 3 hours
  2. filtrationthen filtered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5c278c5d6f1048868f6350bce6f06752
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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