Pyridine → HCID 21935158, compound

HRID 1242780Notes

Reaction equation

HRID 1242780 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][CH:11]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:22][S:23](NC1C=CC=CC=1N1CCN(C(OC(C)(C)C)=O)CC1)(=[O:25])=[O:24].CS(Cl)(=O)=O.N1C=CC=CC=1>>[CH2:1]([CH:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][CH:11]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][S:23]([CH3:22])(=[O:25])=[O:24])[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 21935212Tert-Butyl 4-(2-[(Methylsulfonyl)Amino]Phenyl)-PiperazinecarboxylateHCID 219352252-[2,5-Diaza-5-benzylbicyclo[2.2.1]hept-2-yl]-phenylamine

Product 1

HCID 21935158HCID 21935158, compound

Procedure

{2-[2,5-Diaza-5-benzylbicyclo[2.2.1]hept-2-yl]phenyl}-(methylsulfonyl)amine was prepared from 2-[2,5-diaza-5-benzylbicyclo[2.2.1]hept-2-yl]phenylamine (Step 2) (690 mg, 2.5 mmol) according to the procedure for Preparation III using methanesulfonyl chloride (190 μl, 2.46 mmol) and pyridine (220 μl, 2.72 mmol). The crude mix was purified by flash chromatography (SiO2, 3% MeOH in CH2Cl2) to afford the desired sulfonamide (533 mg). MS (ESI, pos. ion) m/z: 358 (M+H), (ESI, neg. ion) m/z: 356 (M−H). Calc'd for Cl9H23N3O2S: 357.47.

Workup

  1. additionThe crude mix
  2. customwas purified by flash chromatography (SiO2, 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-41a9f74f07614ff2ac06df3f9a32a3e9
Source dataset
uspto-grants-2006_10
Patent number
US07115607B2

Reaction notes

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