HCID 66936842, compound → HCID 178511594, compound

HRID 1623295Notes

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 lyphilization, 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, 4H) 2.18 (t, J=13.77 Hz, 4H) 3.11-3.24 (m, 1H) 3.62-3.76 (m, 1H) 4.72 (s, 2H) 6.95 (s, 1H) 7.12 (d, J=9.96 Hz, 1H) 7.17-7.24 (m, 1H) 7.27-7.37 (m, 1H) 7.40 (s, 1H) 7.42-7.48 (m, 1H) 7.69 (s, 1H) 7.87 (d, J=6.74 Hz, 1H)

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-bdac8ff01fd9455990dbf02bbc258f47
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778951B2

Reaction notes

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