Trifluoroacetic acid → HCID 69299467, compound

HRID 1257157Notes

Reaction equation

COC1C=CC([CH2:7][N:8](C)[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:21]4[CH:26]=[C:25]([NH2:27])[C:24]([F:28])=[CH:23][C:22]=4[CH3:29])[C:15](=[O:20])[N:16]3[CH3:19])=[CH:11][N:10]=2)=CC=1.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>>[NH2:27][C:25]1[C:24]([F:28])=[CH:23][C:22]([CH3:29])=[C:21]([C:14]2[C:15](=[O:20])[N:16]([CH3:19])[C:17]3[C:12]([CH:13]=2)=[CH:11][N:10]=[C:9]([NH:8][CH3:7])[CH:18]=3)[CH:26]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 10340Sodium Carbonate

HCID 69297936HCID 69297936, compound

Product 1

HCID 69299467HCID 69299467, compoundYield 64%

Procedure

7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (1.86 g, 4.3 mmol) and TFA (9.5 mL, 121 mmol) were combined and stirred at RT overnight. The mixture was treated slowly with 2M Na2CO3 until the mixture was just faintly basic, then stirred at RT for 1 h. The solids were collected by filtration, washed thoroughly with H2O, dried partially in the air and then under high vacuum at 65° C. The crude product was purified by flash column chromatography (THF/EtOAc) to afford 3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (0.86 g, 64% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.35 (s, 1H), 7.58 (s, 1H), 6.99 (q, J=4.8 Hz, 1H), 6.56 (d, J=12.0 Hz, 1H), 6.56 (d, J=9.2 Hz, 1H), 6.15 (s, 1H), 4.87 (br s, 2H), 3.48 (s, 3H), 2.84 (d, J=5.2 Hz, 3H), 1.94 (s, 3H); MS (ESI) m/z: 313.2 [M+H]+.

Workup

stirringstirred at RT for 1 h
filtrationThe solids were collected by filtration
washwashed thoroughly with H2O
customdried partially in the air
customat 65° C
customThe crude product was purified by flash column chromatography (THF/EtOAc)

Sources & evidence

ORD record: ord-ed5a1298f43441559a829f789402cfa5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461179B1

Reaction notes

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