1,2-Diaminocyclohexane, trans- → HCID 52914387, compound

HRID 594963Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[NH:14][N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1.Br[C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>O1CCOCC1.CCOC(C)=O.[Cu](I)I>[CH3:29][N:24]([C:21]1[CH:22]=[CH:23][C:18]([N:14]2[C:12]3=[N:13][C:8]([NH:7][C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)=[N:9][CH:10]=[C:11]3[CH:16]=[N:15]2)=[CH:19][CH:20]=1)[S:25]([CH3:28])(=[O:26])=[O:27]

Participants

Conditions

Temperature: 160 °C

Procedure

A suspension of N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (see Example 1, step (i)) (60 mg, 0.28 mmol), N-(4-bromophenyl)-N-methylmethanesulfonamide (1.1 eq), copper iodide (0.1 eq), potassium phosphate (2 eq) and trans-1,2-diaminocyclohexane (0.1 eq) in dioxane (2 mL) was heated in the microwave at 160° C. for 2 h. After cooling to rt the mixture was diluted with EtOAc and washed with water. The organic phase was collected, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography (petroleum ether: EtOAc) to give the title product. 1H NMR (d6-DMSO) δ 10.07 (s, 1H), 9.03 (s, 1H), 8.33 (s, 1H), 8.19 (d, 2H), 7.97 (s, 1H), 7.66 (d, 2H), 7.60 (s, 1H), 3.84 (s, 3H), 3.01 (s, 3H); LC-MS method B, (ES+) 399.1, RT=8.18 min.

Workup

temperatureAfter cooling to rt the mixture
washwashed with water
customThe organic phase was collected
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe resultant residue was purified by column chromatography (petroleum ether: EtOAc)

Sources & evidence

ORD record: ord-38591bbc083542338292cb55b7285a43
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242987B2

Reaction notes

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