Sodium Hydroxide → HCID 44556181, compound

HRID 222000Notes

Reaction equation

FC(F)(F)C([NH:5][C:6]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][C:24]4[C:23]5=[N:33][N:34]=[C:35]([C:36]6[N:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[N:22]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:13][CH:12]=2)[CH2:9][CH:8]([OH:10])[CH2:7]1)=O.[OH-].[Na+]>CCO.O>[NH2:5][C:6]1([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][C:24]4[C:23]5=[N:22][C:35]([C:36]6[N:37]=[CH:38][CH:39]=[CH:40][N:41]=6)=[N:34][N:33]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:15][CH:16]=2)[CH2:9][CH:8]([OH:10])[CH2:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2,2,2-trifluoro-N-(3-hydroxy-1-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-3) (10 mg, 0.016 mmol) in EtOH (1.0 mL) was added NaOH (2M in water, 1.0 mL, 2.00 mmol), and the mixture was heated under microwave irradiation at 100° C. for 1 hour. The mixture was diluted with water, extracted with CHCl3, washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by preparative TLC, eluting with 10% MeOH in CHCl3 to give 3-amino-3-{-4-[9-phenyl-2-(2-pyrimidinyl)[1,2,4]triazolo[5,1-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanol (6-1) as a colorless solid. MS (M+H)+: observed=486, calculated=486.

Workup

extractionextracted with CHCl3
washwashed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by preparative TLC
washeluting with 10% MeOH in CHCl3

Sources & evidence

ORD record: ord-7b837f56d5f04ea2a202ae3846445199
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207169B2

Reaction notes

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