Cyclohexanemethylamine → HCID 178511660, compound

HRID 1623272Notes

Reaction equation

HRID 1623272 reaction equation
[Cl:1][C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18](F)[N:17]=2)=[N:4][C:5]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[CH:23]1([CH2:29][NH2:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CS(C)=O>[Cl:1][C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:30][CH2:29][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[N:17]=2)=[N:4][C:5]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 76688CyclohexanemethylamineHCID 178511659HCID 178511659, compound

Product 1

HCID 178511660HCID 178511660, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
105 °C

Procedure

A mixture of trans-N1-(5-chloro-4-(6-fluoropyridin-2-yl)pyrimidin-2-yl)cyclohexane-1,4-diamine (12 mg, 0.037 mmol), cyclohexylmethanamine (42.2 mg, 0.373 mmol), and DMSO (0.35 ml) was stirred at about 105° C. for about 24 hours. The excess cyclohexylmethanamine was removed under vacuum to yield a residue. The residue was mixed with 0.5 ml DMSO, filtered, purified by prep HPLC and then lyapholized to yield 9.4 mg of the title compound as a TFA salt. LCMS (m/z): 415.3 (MH+), retention time=0.67 min.; 1H NMR (400 MHz, METHANOL-d4, 45° C.) δ ppm 0.89-1.07 (m, 2H) 1.10-1.30 (m, 3H) 1.30-1.54 (m, 4H) 1.55-1.65 (m, 2H) 1.69 (d, J=12.91 Hz, 2H) 1.76 (d, J=12.91 Hz, 2H) 1.96-2.14 (m, 4H) 2.98-3.10 (m, 1H) 3.18 (d, J=6.65 Hz, 2H) 3.71-3.82 (m, 1H) 7.03 (d, J=9.00 Hz, 1H) 7.49 (br. s., 1H) 7.83 (t, J=8.22 Hz, 1H) 8.35 (s, 1H)

Workup

  1. customThe excess cyclohexylmethanamine was removed under vacuum
  2. customto yield a residue
  3. filtrationfiltered
  4. custompurified by prep HPLC

Sources & evidence

ORD record
ord-a77534e025ea4316bb492a2af65ad621
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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