Hydrochloric Acid → Trifluoroacetic acid

HRID 75215Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[N:13](C2CCCCO2)[N:12]=[C:11]([C:20]([F:23])([F:22])[F:21])[C:10]=1[C:24]1[NH:25][C:26]2[C:32]3[CH:33]=[CH:34][N:35]=[CH:36][C:31]=3[NH:30][C:29]3[N:37]=[CH:38][CH:39]=[CH:40][C:28]=3[C:27]=2[N:41]=1.Cl>CO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[NH:13][N:12]=[C:11]([C:20]([F:23])([F:22])[F:21])[C:10]=1[C:24]1[NH:25][C:26]2[C:32]3[CH:33]=[CH:34][N:35]=[CH:36][C:31]=3[NH:30][C:29]3[N:37]=[CH:38][CH:39]=[CH:40][C:28]=3[C:27]=2[N:41]=1.[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-[5-methyl-1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]-3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4′,3′-f]azepine trifluoroacetate (715 mg, 1.23 mmol) in methanol (16 mL) was added 1.25 mL concentrated HCl and the reaction was stirred at 50° C. for 3 h. The reaction was reduced in vacuo and then purified by preparative LCMS to obtain the desired product as a bis-TFA salt (548 mg, 73%). 1H NMR (400 MHz, DMSO-d6): δ 13.8 (bs, 1H), 8.60 (bs, 1H), 8.10 (d, 1H), 8.01 (s, 1H), 7.94 (dd, 1H), 7.61 (m, 2H), 6.88 (dd, 1H), 2.35 (s, 3H). 19F NMR (400 MHz, DMSO-d6): δ-59.476 (3F), −74.791 (6F). MS (EI) m/z=384. (M+H).

Workup

custompurified by preparative LCMS

Sources & evidence

ORD record: ord-5da88b0b06974c5f9df6442333da435f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835423B2

Reaction notes

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