O-Phenylenediamine → N-(2-Amino-phenyl)-4-[(4-methanesulfonyl-phenylamino)-methyl]-benzamide

HRID 852939Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:22]1([NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28]>>[NH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:29][C:17](=[O:19])[C:16]1[CH:15]=[CH:14][C:13]([CH2:12][NH:11][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=2)=[CH:21][CH:20]=1

Participants

Reactant 2

HCID 7243O-Phenylenediamine

HCID 434532894-[(4-Methanesulfonyl-phenylamino)-methyl]-benzoic acid

Product 1

HCID 66622022N-(2-Amino-phenyl)-4-[(4-methanesulfonyl-phenylamino)-methyl]-benzamide

Procedure

The compound was obtained by reacting the acid 211a with 1,2-phenylenediamine following the procedure described in the scheme 1, step 5 (example 1). 1H NMR: (DMSO) δ (ppm): 9.57 (bs, 1H), 7.90 (d, J=8.4 Hz, 1H), 7.50 (d, J=8.2 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.35 (t, J=6.0 Hz, 1H), 7.11 (d, J=7.6 Hz, 1H), 6.93 (dt, J=1.6, 8.0 Hz, 1H), 6.73 (dd, J=1.6, 8.0 Hz, 1H), 6.66 (d, J=8.8 Hz, 2H), 6.55 (dt, J=1.2, 7.6 Hz, 1H), 4.88 (bs, 2H), 4.43 (d, J=6.0 Hz, 2H). LRMS: (calc.) 395.5; (obt.) 396.4 (MH)+.

Workup

customThe compound was obtained

Sources & evidence

ORD record: ord-639f8d979e8b4a90813c56ebe25e1b38
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253204B2

Reaction notes

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