Ethyl Acetate → N3,N3-dimethyl-1-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-1,3-cyclobutanediamine

HRID 221991Notes

Reaction equation

[CH3:1][N:2]([CH3:45])[CH:3]1[CH2:6][C:5]([NH:38]C(=O)C(F)(F)F)([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][C:20]4[C:19]5=[N:29][N:30]=[C:31]([C:32]6[N:37]=[CH:36][CH:35]=[CH:34][N:33]=6)[N:18]5[CH:17]=[CH:16][C:15]=4[N:14]=3)=[CH:9][CH:8]=2)[CH2:4]1.[OH-].[K+].CCOC(C)=O.C([O-])(O)=O.[Na+]>CCO.[Cl-].[Na+].O>[CH3:1][N:2]([CH3:45])[CH:3]1[CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][C:20]4[C:19]5=[N:29][N:30]=[C:31]([C:32]6[N:37]=[CH:36][CH:35]=[CH:34][N:33]=6)[N:18]5[CH:17]=[CH:16][C:15]=4[N:14]=3)=[CH:9][CH:8]=2)([NH2:38])[CH2:6]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of N-(3-(dimethylamino)-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)-2,2,2-trifluoroacetamide (4-4) (10 mg, 0.016 mmol) in EtOH (1.0 mL) was added KOH (1M in water, 0.1 mL, 0.10 mmol), and the mixture was heated under microwave irradiation at 100° C. for 40 minutes. To the mixture was added EtOAc, sat. NaHCO3, and brine. The resulting solid was collected by filtration to give N3,N3-dimethyl-1-{4-[9-phenyl-3-(2-pyrimidinyl)-[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-1,3-cyclobutanediamine (4-5) as colorless solid. HRMS (M+H)+: observed=513.2515, calculated=513.2510.

Workup

filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record: ord-66166fe6923842d8aa321087cc9d6a64
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207169B2

Reaction notes

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