2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 178509395, compound

HRID 1505946Notes

Reaction equation

HRID 1505946 reaction equation
[C:1]([C:3]1[N:11]=[CH:10][C:9]2[NH:8][C:7]3[N:12]=[CH:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)=[CH:18][CH:17]=4)=[CH:15][C:6]=3[C:5]=2[CH:4]=1)#[N:2].C1(C2[O:37]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C(Cl)Cl>[C:1]([C:3]1[N:11]=[CH:10][C:9]2[NH:8][C:7]3=[N+:12]([O-:37])[CH:13]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([CH2:22][N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)=[CH:20][CH:21]=4)[CH:15]=[C:6]3[C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 44545757HCID 44545757, compound

Product 1

HCID 178509395HCID 178509395, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-cyano-3-(4-piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (110 mg, 0.30 mmol) and 3-phenyl-2-(phenylsulfonyl)oxaziridine (102 mg, 0.39 mmol) in DCM (5.8 mL) was stirred at room temperature for 2 h. The solid was collected by filtration and washed with DCM (3×20 mL) to afford a bright yellow solid (100 mg, 90%). NMR (400 MHz, DMSO-D6): 8.98 (s, 1H), 8.91 (s, 1H), 8.90 (s, 1H), 8.83 (s, 1H), 7.66 (m, 4H), 4.43 (s, 2H), 3.13 (m, 2H), 2.14 (m, 2H), 1.59 (m, 4H), 1.34 (m, 2H). LCMS (method D): RT=8.82 min, M+H+=384.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with DCM (3×20 mL)

Sources & evidence

ORD record
ord-19354610bf8a4a1fb0fd7b217143b476
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

Loading…