1,4-Diaminocyclohexane → HCID 178513795, compound

HRID 1623337Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:9]2[N:10]=[C:11]([NH:18][CH2:19][CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[C:12]([C:15]([NH2:17])=[O:16])=[N:13][CH:14]=2)=[CH:4][C:5](F)=[N:6][CH:7]=1.[NH2:26][CH:27]1[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1>CS(C)=O>[NH2:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([NH:33][C:5]2[CH:4]=[C:3]([C:9]3[N:10]=[C:11]([NH:18][CH2:19][CH:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:12]([C:15]([NH2:17])=[O:16])=[N:13][CH:14]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 100 °C

Procedure

5-(5-chloro-2-fluoropyridin-4-yl)-3-((tetrahydro-2H-pyran-4-yl)methyl)aminopyrazine-2-carboxamide (0.035 g, 0.096 mmol) was dissolved in DMSO (2 ml). This was treated with 1,4-diaminocyclohexane (0.109 g, 0.957 mmol). The reaction mixture was then heated at 100° C. for 4 hr. The material was purified by preparative reverse-phase HPLC to give 0.0053 g of 5-(2-(trans-4-aminocyclohexylamino)-5-chloropyridin-4-yl)-3-((tetrahydro-2H-pyran-4-yl)methyl)aminopyrazine-2-carboxamide as the TFA salt. LCMS (m/z): 460.1 (MH+), retention time=0.54 min.

Workup

customThe material was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-977b6926d8ee4801a1c6d135cec2a9c8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778951B2

Reaction notes

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