3-Fluorobenzylamine → HCID 178511266, compound

HRID 1963858Notes

Reaction equation

[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18](F)[N:17]=3)[C:13]([Cl:23])=[CH:12][N:11]=2)[CH2:5][CH2:4]1.[F:24][C:25]1[CH:26]=[C:27]([CH2:31][NH2:32])[CH:28]=[CH:29][CH:30]=1>CS(C)=O>[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:32][CH2:31][C:27]4[CH:28]=[CH:29][CH:30]=[C:25]([F:24])[CH:26]=4)[N:17]=3)[C:13]([Cl:23])=[CH:12][N:11]=2)[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of N-(trans-4-(aminomethyl)cyclohexyl)-5′-chloro-6-fluoro-2,4′-bipyridin-2′-amine (15 mg, 0.045 mmol), DMSO (0.35 ml), TEA (0.012 ml, 0.090 mmol) and (3-fluorophenyl)methanamine (50.5 mg, 0.403 mmol) reaction mixture was flushed with argon and then stirred at about 105° C. for about 40 hours. The excess (3-fluorophenyl)methanamine was removed under reduced pressure to yield a crude material, which was mixed with 0.5 ml DMSO, filtered, purified by prep LC, and then lyophilized to yield 11.2 mg of the title compound, as a TFA salt. LCMS (m/z): 440.2(MH+), retention time=0.62 min. 1H NMR (300 MHz, METHANOL-d4, 25° C.) δ ppm 1.11-1.28 (m, 2 H) 1.28-1.47 (m, 2 H) 1.67 (ddd, J=10.92, 7.40, 3.66 Hz, 1 H) 1.92 (d, J=11.72 Hz, 2 H) 2.14 (d, J=10.55 Hz, 2 H) 2.83 (d, J=6.74 Hz, 2 H) 3.57-3.69 (m, 1 H) 4.63 (s, 2 H) 6.84 (d, J=8.79 Hz, 1 H) 6.90 (s, 1 H) 6.94 (d, J=7.03 Hz, 1 H) 6.96-7.03 (m, 1 H) 7.10 (d, J=9.96 Hz, 1 H) 7.18 (d, J=7.62 Hz, 1 H) 7.29-7.39 (m, 1 H) 7.69-7.77 (m, 1 H) 8.01 (s, 1 H)

Workup

customwas flushed with argon
customThe excess (3-fluorophenyl)methanamine was removed under reduced pressure
customto yield a crude material, which
filtrationfiltered
custompurified by prep LC

Sources & evidence

ORD record: ord-7acfeb443e7a4de1addbdbd557cf6ee8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415381B2

Reaction notes

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