Potassium Carbonate → HCID 178504891, compound

HRID 1623309Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=4)[N:16]=3)[C:12]([Cl:30])=[CH:11][N:10]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].CS(O[CH2:42][CH2:43][S:44]([CH3:47])(=[O:46])=[O:45])(=O)=O>CS(C)=O>[Cl:30][C:12]1[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[N:16]=2)=[CH:14][C:9]([NH:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([NH:1][CH2:42][CH2:43][S:44]([CH3:47])(=[O:46])=[O:45])[CH2:3][CH2:4]2)=[N:10][CH:11]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a scintillation vial containing N2′-(trans-4-aminocyclohexyl)-5′-chloro-N6-(3-fluorobenzyl)-2,4′-bipyridine-2′,6-diamine (10 mg, 0.023 mmol) and K2CO3 (8 mg, 0.058 mmol) was added DMSO (0.5 ml) and 2-(methylsulfonyl)ethyl methanesulfonate (30 mg). The reaction mixture was capped and heated to 120° C. in an oil bath for 4 hr. The resulting solution was purified by reverse phase preparative HPLC to yield 5′-chloro-N6-(3-fluorobenzyl)-N2′-(trans-4-(2-(methylsulfonyl)ethylamino)cyclohexyl)-2,4′-bipyridine-2′,6-diamine (3.7 mg, 24%). LCMS (m/z): 532.2 (MH+), retention time=0.62 min as a TFA salt after lypholyzing.

Workup

customThe reaction mixture was capped
customThe resulting solution was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-e7401d4cd9ca45ac987349c5e1e83bfa
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778951B2

Reaction notes

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