Trifluoroacetic acid → (6-methoxy-pyridin-3-ylmethyl)-[5-(5H-pyrrolo[2,3-b]pyrazin-7-ylmethyl)-pyridin-2-yl]-amine

HRID 1642094Notes

Reaction equation

C(OC(=O)[N:7]([C:17]1[CH:22]=[CH:21][C:20]([CH:23](O)[C:24]2[C:32]3[C:27](=[N:28][CH:29]=[CH:30][N:31]=3)[NH:26][CH:25]=2)=[CH:19][N:18]=1)[CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:16][O:15][C:12]1[N:11]=[CH:10][C:9]([CH2:8][NH:7][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]3[C:32]4[C:27](=[N:28][CH:29]=[CH:30][N:31]=4)[NH:26][CH:25]=3)=[CH:19][N:18]=2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To {5-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (7, 0.220 g, 0.48 mmol) in 10.4 mL of acetonitrile, triethylsilane (2.1 mL 0.013 mol) and trifluoroacetic acid (1.0 mL 0.014 mol) were added. The reaction was heated to 80° C. for 4 hours, then poured into aqueous potassium carbonate, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and purified by silica gel column chromatography eluting with methanol:dichloromethane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a white solid (P-0001, 63.4 mg, 38.5%). MS (ES1): [M+H+]+=347.0.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under vacuum
custompurified by silica gel column chromatography
washeluting with methanol
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-6a5c2716f2154814a509953d19b95d2c
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119637B2

Reaction notes

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