Trifluoroacetic acid → HCID 58588426, compound

HRID 1361703Notes

Reaction equation

[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[C:10]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:39])[CH:24]([NH:31]C(=O)OC(C)(C)C)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:18][CH:17]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>>[NH2:31][CH:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:10]2[C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([NH:2][CH3:1])[N:8]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:17][CH:18]=1)=[O:39]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 516892Sodium Bicarbonate

HCID 91563378HCID 91563378, compound

Product 1

HCID 58588426HCID 58588426, compound

Procedure

Tert-butyl (rac)-2-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenylamino)-2-oxo-1-phenylethylcarbamate (0.040 g, 0.076 mmol) was treated with 1 mL TFA at ambient temperature. After 16 h, saturated aqueous sodium bicarbonate was added until pH=9, and the aqueous layer extracted once with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give (rac)-2-amino-N-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-2-phenylacetamide. MS m/z=441 [M+1]+. Calc'd for C25H24N6O2: 440.51.

Workup

extractionthe aqueous layer extracted once with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8fecd11f3a914c3bbd6586a7d2389d38
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880000B2

Reaction notes

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