HCID 66936842, compound → HCID 178511594, compound

HRID 1963875Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[C@H:27]1([NH2:34])[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29][CH2:28]1>CS(C)=O>[NH2:33][C@H:30]1[CH2:31][CH2:32][C@H:27]([NH:34][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[C:12]([C:14]([F:15])([F:17])[F:16])[CH:11]=[C:10]([NH:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=4)[N:9]=3)[CH:5]=[CH:4][N:3]=2)[CH2:28][CH2:29]1

Participants

Conditions

Temperature: 105 °C

Procedure

To 2′-fluoro-N-(3-fluorobenzyl)-4-(trifluoromethyl)-2,4′-bipyridin-6-amine (34 mg, 0.093 mmol) was added DMSO (1.7 ml) and trans-cyclohexane-1,4-diamine (159 mg, 1.396 mmol). The resulting reaction mixture was stirred at 105° C. until completion as indicated by LCMS, about 40 hours. To the crude reaction mixture was added 0.75 ml of DMSO, filtered and purified by prep LC. After lyophilization, 28.1 mg of the title compound was obtained as a TFA salt. LCMS (m/z): 460.3 (MH+), retention time=0.72 min.; 1H NMR (300 MHz, METHANOL-d4, 25° C.) δ ppm 1.40-1.72 (m, 4 H) 2.18 (t, J=13.77 Hz, 4 H) 3.11-3.24 (m, 1H) 3.62-3.76 (m, 1 H) 4.72 (s, 2 H) 6.95 (s, 1 H) 7.12 (d, J=9.96 Hz, 1 H) 7.17-7.24 (m, 1 H) 7.27-7.37 (m, 1 H) 7.40 (s, 1 H) 7.42-7.48 (m, 1 H) 7.69 (s, 1 H) 7.87 (d, J=6.74 Hz, 1 H)

Workup

customThe resulting reaction mixture
customas indicated by LCMS, about 40 hours
customTo the crude reaction mixture
filtrationfiltered
custompurified by prep LC

Sources & evidence

ORD record: ord-be121e5aa95c4866ab4fb415d88e9433
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415381B2

Reaction notes

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