Cesium carbonate → ethyl 2-(3-(5-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-pyrazol-1-yl)piperidin-1-yl)-2-methylpropanoate

HRID 1530674Notes

Reaction equation

HRID 1530674 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([C:22]5[N:23]([CH:27]6[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]6)[N:24]=[CH:25][CH:26]=5)=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:33]=2)=[N:7][C:6]([CH3:34])=[N:5]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:42]([CH3:49])([CH3:48])[C:43]([O:45][CH2:46][CH3:47])=[O:44]>CN(C)C=O>[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([C:22]5[N:23]([CH:27]6[CH2:32][CH2:31][CH2:30][N:29]([C:42]([CH3:49])([CH3:48])[C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:28]6)[N:24]=[CH:25][CH:26]=5)=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:33]=2)=[N:7][C:6]([CH3:34])=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 683130012-(2-Isopropyl-5-methyl-1,2,4-triazol-3-yl)-9-[2-(3-piperidyl)pyrazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

Product 1

HCID 68312882ethyl 2-(3-(5-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-pyrazol-1-yl)piperidin-1-yl)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(2-isopropyl-5-methyl-1,2,4-triazol-3-yl)-9-[2-(3-piperidyl)pyrazol-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine; I; 100 mass % in N,N-Dimethylformamide; 100 mass % was added Cesium Carbonate; 2.00 equiv.; 1.090 mmol; 100 mass % followed by ethyl 2-bromo-2-methyl-propanoate; G; 3.00 equiv.; 1.635 mmol; 100 mass %. The reaction mixture was heated to 90° C. and was stirred for 12 hours. LC-MS analysis of the reaction mixture showed almost complete conversion to the desired product. The solvent was removed and the residue was purified on silica gel (0→10% MeOH/DCM) to yield ethyl 2-(3-(5-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-pyrazol-1-yl)piperidin-1-yl)-2-methylpropanoate as a light yellow foam.

Sources & evidence

ORD record
ord-264a0260d561442e9770e65912502915
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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