1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67500317, compound

HRID 513274Notes

Reaction equation

HRID 513274 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([C:11]([NH2:13])=[O:12])=[CH:9][N:8]=[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[CH:6]=1)[C:2]#[CH:3].[N:27]([CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[N+:28]=[N-:29].C1CCN2C(=NCCC2)CC1>CO.[Cu]I>[N:32]1([CH2:31][CH2:30][N:27]2[CH:3]=[C:2]([CH2:1][NH:4][C:5]3[C:10]([C:11]([NH2:13])=[O:12])=[CH:9][N:8]=[C:7]([NH:14][C:15]4[CH:20]=[CH:19][C:18]([CH:21]5[CH2:22][CH2:23][O:24][CH2:25][CH2:26]5)=[CH:17][CH:16]=4)[CH:6]=3)[N:29]=[N:28]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27372091-(2-azidoethyl)piperidineHCID 86664542HCID 86664542, compound

Product 1

HCID 67500317HCID 67500317, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Procedure

Compound 4-(prop-2-ynylamino)-6-(4-(tetrahydro-2H-pyran-4-yl)phenylamino)nicotinamide (Example 184) (20 mg, 0.057 mmol) was dissolved in 6 mL MeOH. To it were added 1-(2-azidoethyl)piperidine (18 mg, 0.11 mmol), DBU (26 μL, 0.17 mmol) and finally powder CuI (13 mg, 0.068 mmol). The mixture was stirred at RT for 5 h, filtered and subjected to reverse phase prep HPLC to isolate the title compound. MS found for C27H36N8O2 as (M+H)+ 505.4. UV: λ=259 nm. 1H NMR: (CD3OD) δ 8.14 (1H, s), 8.12 (1H, s), 7.39 (2H, dt, J=8.4; 2.0 Hz), 7.24 (2H, dt, J=8.4; 2.0 Hz), 6.20 (1H, s), 4.60 (2H, s), 4.05 (2H, m), 3.73 (2H, m), 3.59 (4H, m), 3.04 (2H, m), 2.87 (1H, m), 1.95 (2H, m), 1.86-1.75 (8H, m) ppm.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-3889d736b8264f0b9faf78ae92dcf3b4
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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