Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 131727488, compound

HRID 1986097Notes

Reaction equation

F[C:2]1[N:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([N:6]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH3:7])=[O:5].[ClH:19].[NH:20]1[C:24]2=[N:25][CH:26]=[CH:27][C:28]([O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36]C4C(C(NC5C=CC(F)=CC=5F)=O)=CN=CC=4)=[CH:32][C:31]=3[F:54])=[C:23]2[CH:22]=[CH:21]1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CC(N(C)C)=O>[ClH:19].[ClH:19].[NH:20]1[C:24]2=[N:25][CH:26]=[CH:27][C:28]([O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:2]4[N:18]=[CH:17][CH:16]=[CH:15][C:3]=4[C:4]([N:6]([C:8]4[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=4)[CH3:7])=[O:5])=[CH:32][C:31]=3[F:54])=[C:23]2[CH:22]=[CH:21]1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 2-fluoro-N-(4-fluorophenyl)-N-methylnicotinamide (50 mg, 0.2 mmol) and 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluoroaniline (122 mg, 0.5 mmol, Compound C of Example 1) in DMA (0.8 mL) was heated in a microwave at 160° C. for 20 min. The product was purified by preparative (RP) HPLC to afford the title compound as a beige solid (11 mg, 11% yield)—dihydrochloride salt. 1H NMR (CD3OD) δ 8.56 (d, 1H, J=3.5 Hz), 8.23 (dd, 1H, J=7.6, 1.0 Hz), 8.19 (d, 1H, J=7.1 Hz), 7.58 (m, 3H), 7.32 (dd, 1H, J=11.2, 2.5 Hz), 7.22 (d, 1H, J=8.6 Hz), 7.04 (d, 1H, J=4.1 Hz), 6.96 (d, 1H, J=7.9 Hz), 6.47 (m, 4H), 3.27 (s. 3H). MS(ESI+) m/z 472 (M+H)+.

Workup

customThe product was purified by preparative (RP) HPLC

Sources & evidence

ORD record: ord-eccd2919307945ed847fc368bb351a9a
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547782B2

Reaction notes

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