4-(Difluoromethoxy)aniline → 1-[(6-Aminopyridin-3-yl)methyl]-3-{[4-(difluoromethoxy)phenyl]amino}-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113774Notes

Reaction equation

Cl[C:2]1[C:3](=[O:29])[N:4]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21]C(=O)OC(C)(C)C)=[N:19][CH:20]=2)[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:30][CH:31]([F:40])[O:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1>CN(C=O)C>[NH2:21][C:18]1[N:19]=[CH:20][C:15]([CH2:14][N:4]2[C:5](=[O:13])[C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[C:2]([NH:37][C:36]3[CH:38]=[CH:39][C:33]([O:32][CH:31]([F:30])[F:40])=[CH:34][CH:35]=3)[C:3]2=[O:29])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of tert-butyl {5-[(3-chloro-2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-1-yl)methyl]pyridin-2-yl}carbamate ( 0.70 g, 1.7 mmol) and 4-(difluoromethoxy)-aniline (0.54 g, 3.4 mmol) in DMF (4 mL) was heated in a microwave reactor at 150° C. for eight min. The solvent was evaporated and the residue was purified on a column (Isolute® SI, 10 g/70 mL), using CH2Cl2 and then CH3OH/CH2Cl2 (1:99, 2:98 and then 5:95) as eluant, to give 0.4 g (54%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.99 (bs, 1H), 7.67-7.62 (m, 2H), 7.14-7.04 (m, 3H), 6.91 (d, J=8 Hz, 2H), 6.78 (d, J=8 Hz, 1H), 6.72 (d, J=9 Hz, 2H), 6.63 (d, J=9 Hz, 2H), 6.33 (t, J=74 Hz, 1H), 4.60 (s, 2H).

Workup

customThe solvent was evaporated
customthe residue was purified on a column (Isolute® SI, 10 g/70 mL)

Sources & evidence

ORD record: ord-e10555f810a34eca897e0e30eac173dc
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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