O-Phenylenediamine → HCID 11667307, compound

HRID 1988792Notes

Reaction equation

[N:1]1([CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C1CN([P+](O[N:37]2N=[N:44][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]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>[N:1]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[NH2:44])=[O:17])=[CH:18][CH:19]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 4-((1H-benzo[d]imidazol-1-yl)methyl)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 4-((1H-benzo[d]imidazol-1-yl)methyl)-N-(2-aminophenyl)benzamide. 1H NMR (400 MHz, DMSO-D6) δ ppm 4.88 (s, 2H), 5.60 (s, 2H), 6.54-6.61 (m, 1H), 6.76 (d, J=8.08 Hz, 1H), 6.93-6.98 (m, 1H), 7.13 (d, J=7.58 Hz, 1H), 7.18-7.23 (m, 2H), 7.43 (d, J=8.34 Hz, 2H), 7.48-7.54 (m, 1H), 7.65-7.70 (m, 1H), 7.93 (d, J=8.08 Hz, 2H), 8.46 (s, 1H), 9.60 (s, 1H). ESI-MS: m/z 343.3 (M+H)+.

Workup

filtrationthe reaction was filtered
customthe crude material was purified by HPLC

Sources & evidence

ORD record: ord-7d93dd131c5347c9ad4ccd8bb4515bfe
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642275B2

Reaction notes

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