Cyclohexanemethylamine → HCID 178511588, compound

HRID 1963851Notes

Reaction equation

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

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of trans-N1-(6-fluoro-2,4′-bipyridin-2′-yl)cyclohexane-1,4-diamine (15 mg, 0.052 mmol), DMSO (0.4 ml), and cyclohexylmethanamine (59.3 mg, 0.524 mmol) was heated at about 105° C. for about 24 hours, or until the product pormation was completed, as indicated by LCMS. The excess amine was removed under reduced pressure to yield a residue. The residue was mixed with 0.5 ml of DMSO, filtered and purified by prep LC. After lyophilization, 11.3 mg of the title compound was obtained as a TFA salt. LCMS (m/z): 380.3 (MH+), retention time=0.61 min. 1H NMR (400 MHz, METHANOL-d4, 45° C.) δ ppm 0.97-1.11 (m, 2 H) 1.17-1.36 (m, 3 H) 1.49-1.72 (m, 6 H) 1.71-1.80 (m, 2 H) 1.84 (d, J=12.91 Hz, 2 H) 2.11-2.28 (m, 4 H) 3.13-3.25 (m, 1 H) 3.28 (d, 2 H, App.) 3.65-3.75 (m, 1 H) 6.65 (d, J=8.61 Hz, 1 H) 7.16 (d, J=7.43 Hz, 1 H) 7.43-7.48 (m, 1 H) 7.52 (t, J=7.83 Hz, 1 H) 7.64 (s, 1 H) 7.85 (d, J=7.04 Hz, 1 H)

Workup

customThe excess amine was removed under reduced pressure
customto yield a residue
filtrationfiltered
custompurified by prep LC

Sources & evidence

ORD record: ord-708667352fac433fa1b1a3034e23eb6b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415381B2

Reaction notes

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