Trifluoroacetic acid → 3-aminomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one trifluoroacetate salt

HRID 1887788Notes

Reaction equation

C(NC(=O)O)(C)(C)C.C(NC(=O)O)(C)(C)C.[NH2:17][CH2:18][C:19]1[C:28](=[O:29])[C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:20]=1[C:36]1[O:37][CH:38]=[CH:39][N:40]=1.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>C(Cl)Cl>[F:44][C:43]([F:46])([F:45])[C:41]([OH:47])=[O:42].[NH2:17][CH2:18][C:19]1[C:28](=[O:29])[C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:20]=1[C:36]1[O:37][CH:38]=[CH:39][N:40]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-aminomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one bis(tert-butyl carbamate) (26 mg, 50.1 μmol) in methylene chloride (167 μL) at 25° C. was treated with TFA (83.6 μL). The reaction was stirred at 25° C. for 4 hr. The reaction was concentrated in vacuo, triturated with diethyl ether and then dried under high vacuum to give 3-aminomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one trifluoroacetate salt. The product was used in subsequent steps without further purification.

Workup

concentrationThe reaction was concentrated in vacuo
customtriturated with diethyl ether
customdried under high vacuum

Sources & evidence

ORD record: ord-9b35ba403c4040b9b029843a4ff72783
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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