O-Phenylenediamine → HCID 11602908, compound

HRID 1988789Notes

Reaction equation

[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[NH:3]1.C1CN([P+](O[N:38]2N=[N:45][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1(N)C=CC=CC=1N.CCN(CC)CC>CN(C=O)C>[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[NH:45][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([CH2:7][N:6]2[C:5]3[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=3[NH:3][C:2]2=[O:1])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 4-(2-Oxo-2,3-dihydro-benzoimidazol-1 -ylmethyl)-benzoic acid (0.1 mmol) in DMF (1 mL) was sequentially treated with PyBOP (0.12 mmol), 1,2-phenylenediamine (0.12 mmol) and Et3N (0.3 mmol). After stirring at 23° C. for 4 h, the reaction was filtered and the crude material was purified by HPLC to yield N-(2-Amino-phenyl)-4-(2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-benzamide. 1H NMR (400 MHz, DMSO-D6) δ ppm 4.88 (s, 2H), 5.09 (s, 2H), 6.55-6.61 (m, 1H), 6.76 (d, J=8.08 Hz, 1H), 6.93-7.04 (m, 5H), 7.14 (d, J=7.58 Hz, 1H), 7.43 (d, J=8.08 Hz, 2H), 7.93 (d, J=8.08 Hz, 2H), 9.61 (s, 1H), 11.02 (s, 1H). ESI-MS: m/z 359.3 (M+H)+.

Workup

filtrationthe reaction was filtered
customthe crude material was purified by HPLC

Sources & evidence

ORD record: ord-e6216c55f82b486ebc82824ab0bbed9c
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642275B2

Reaction notes

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