Trifluoroacetic acid → 4-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-ylamine

HRID 2273236Notes

Reaction equation

FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:24]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[N:22][C:21]([O:33][CH3:34])=[CH:20][CH:19]=2)(C)(C)C>ClCCl>[CH2:26]([O:25][C:24]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:33][CH3:34])[N:22]=2)[N:17]=[CH:16][C:15]=1[NH2:14])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoroacetic acid (10.0 mL, 131.2 mmol, 20.0 eq) is added at 0° C. to a stirred solution of (4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-yl)-carbamic acid tert-butyl ester (2.50 g, 6.55 mmol, 1.0 eq) in dichloromethane (50 mL). After 20 hours stirring at 0° C., the reaction mixture is extracted with dichloromethane (3×200 mL) and water (200 mL) and the pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-ylamine as a light yellow solid (1.70 g, 92% yield).

Workup

extractionthe reaction mixture is extracted with dichloromethane (3×200 mL) and water (200 mL)
additionthe pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-c5abc549abbc43489ca4b9995c80b5b3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120822B2

Reaction notes

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