Methylamine → HCID 178484091, compound

HRID 1623311Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=4)[N:21]=3)[C:17]([Cl:35])=[CH:16][N:15]=2)[CH2:9][CH2:8]1)(=O)=O.[CH3:36][NH2:37]>CO>[Cl:35][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)[N:21]=2)=[CH:19][C:14]([NH:13][C@H:10]2[CH2:11][CH2:12][C@H:7]([CH2:6][NH:37][CH3:36])[CH2:8][CH2:9]2)=[N:15][CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a scintillation vial containing (trans-4-(5′-chloro-6-(3-fluorobenzylamino)-2,4′-bipyridin-2′-yl-amino)cyclohexyl)methyl methanesulfonate (15 mg, 0.029 mmol) was added MeOH (1 ml) and a solution of methyl amine (0.14 ml, 0.289 mmol) in MeOH. The reaction mixture was capped and heated to 70° C. in a oil bath for 16 hr. The resulting solution was concentrated and purified by reverse phase preparative HPLC to yield 5′-chloro-N6-(3-fluorobenzyl)-N2′-(trans-4-((methylamino) methyl)cyclohexyl)-2,4′-bipyridine-2′,6-diamine (8.6 mg, 52%), LCMS (m/z): 454.2 (MH+), retention time=0.64 min as a TFA salt after lypholyzing. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.15-1.29 (m, 2H) 1.29-1.42 (m, 2H) 1.67-1.80 (m, 1H) 1.86-1.96 (m, 2H) 2.09-2.21 (m, 2H) 2.71 (s, 3H) 2.90 (d, J=7.04 Hz, 2H) 3.58-3.70 (m, 1H) 4.63 (s, 2H) 6.88 (s, 2H) 6.94 (d, J=7.43 Hz, 1H) 6.96-7.03 (m, 1H) 7.07-7.13 (m, 1H) 7.15-7.21 (m, 1H) 7.29-7.39 (m, 1H) 7.69-7.78 (m, 1H) 8.01 (s, 1H).

Workup

customThe reaction mixture was capped
concentrationThe resulting solution was concentrated
custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-8f7889d1951749b78b88a8c4204b45c3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778951B2

Reaction notes

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