(3-Aminophenyl)methanesulfonamide → 3-[[4-(2-Methoxyphenyl)-2-pyridinyl]amino]-benzenemethanesulfonamide

HRID 593287Notes

Reaction equation

HRID 593287 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl[C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH:17]=[CH:16][N:15]=1>CN(C=O)C>[CH3:27][O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][S:9]([NH2:12])(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 13266255(3-Aminophenyl)methanesulfonamideHCID 584326112-Chloro-4-(2-methoxyphenyl)pyridine

Product 1

HCID 601970503-[[4-(2-Methoxyphenyl)-2-pyridinyl]amino]-benzenemethanesulfonamideYield 2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

G2 was prepared from (3-aminophenyl)methanesulfonamide (85 mg, 0.46 mmol) and A1 (100 mg, 0.46 mmol) following the procedure reported for G1 by heating in DMF for 3 hours, and it was obtained as a colorless amorphous solid (3.1 mg, 2%). 1H NMR (400 MHz, d6-DMSO, 300K) δ 3.79 (s, 3H), 4.15 (s, 2H), 6.73 (bs, 2H), 6.84 (dd, J=5.3 Hz, J=1.5 Hz, 1H), 6.96-6.98 (m, 1H), 7.04 (dt, J=1.0 Hz, J=8.0 Hz, 1H), 7.13 (d, J=8.2 Hz, 1H), 7.21-7.25 (m, 2H), 7.33 (dd, J=7.6 Hz, J=1.8 Hz, 1H), 7.36-7.42 (m, 1H), 7.64-7.68 (m, 2H), 8.14 (d, J=5.3 Hz, 1H), 9.08 (s, 1H). MS (ES) C19H19N3O3S requires: 369. found: 370 (M+H)+.

Sources & evidence

ORD record
ord-d1ad620c41384b74a22676e341579bc4
Source dataset
uspto-grants-2016_01
Patent number
US09242937B2

Reaction notes

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