3-Chloro-4-fluoroaniline → HCID 44435431, compound

HRID 2113601Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[F:8].[CH:10]1([NH:15][C:16]2[C:25]3[C:20](=[CH:21][N:22]=[C:23](F)[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:27]#[N:28])[CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][N:22]=2)[N:19]=[CH:18][C:17]([C:27]#[N:28])=[C:16]3[NH:15][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 3-chloro-4-fluorobenzenamine (550 mg, 3.78 mmol, 38 eq), 4-(cyclopentylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile (28 mg, 0.1 mmol, 1 eq), and cesium carbonate (506 mg, 1.55 mmol, 15.5 eq) in DMF (4 mL) was heated to 200° C. in a microwave tube for 1 hr using microwave reactor. Preparative HPLC purification yielded 15 mg product (36% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 1.52-1.68 (m, 2 H) 1.70-1.91 (m, 4 H) 1.99-2.16 (m, 2 H) 4.58-4.76 (m, 1 H) 7.33 (t, J=9.09 Hz, 1 H) 7.45-7.56 (m, 1 H) 7.76 (s, 1 H) 7.80 (d, J=7.07 Hz, 1 H) 7.87-7.97 (m, 1 H) 8.32 (s, 1 H) 8.90 (s, 1 H) 9.64 (s, 1 H).

Workup

customPreparative HPLC purification

Sources & evidence

ORD record: ord-1401c3f7e60b42aaba132bffa835a301
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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