Trifluoroacetic acid → HCID 178425347, compound

HRID 1987052Notes

Reaction equation

C(OC([N:8]=[C:9]([N:11](C(OC(C)(C)C)=O)[O:12][CH2:13][CH2:14][NH:15][C:16](=[O:39])[CH2:17][C:18]1[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[C:20]([NH:26][CH2:27][C:28]([F:37])([F:36])[C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][N:30]=2)[C:19]=1[F:38])[NH2:10])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:9]([NH:11][O:12][CH2:13][CH2:14][NH:15][C:16](=[O:39])[CH2:17][C:18]1[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[C:20]([NH:26][CH2:27][C:28]([F:36])([F:37])[C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][N:30]=2)[C:19]=1[F:38])(=[NH:8])[NH2:10]

Participants

Conditions

Temperature: 0 °C

Procedure

N-[2-(N′,N″-Bis(tert-butoxycarbonyl)amidinoaminooxy)ethyl]-2-{3-[(2,2-difluoro-2-(5-methylpyridyl)ethyl)amino]-6-cyano-2-fluorophenyl}acetamide (832 mg, 1.28 mmol), as prepared in the previous step, was dissolved into CH2Cl2 (6 mL), cooled to 0° C. and treated with TFA (2 mL), then allowed to warm to rt. After 12 h, the reaction was concentrated in vacuo to afford a yellow oil. Purification via flash chromatography (inactivated with NH3, 10% MeOH/CH2Cl2) afforded the product as a white solid (413 mg, 0.92 mmol, 72% yield). 1H NMR (300 Hz, CD3OD) δ 8.49 (s, 1H), 7.73 (d, J=7.9 Hz, 1H), 7.57 (d, J=8.2 Hz, 1H), 7.27 (d, J=8.6 Hz, 1H), 6.82 (t, J=8.2 Hz, 1H), 4.07 (t, J=13.8 Hz, 2H), 3.79 (t, J=5.3 Hz, 2H), 3.72 (d, J=1.98 Hz, 2H), 3.42 (t, J=5.3 Hz, 2H), 2.39 (s, 3H); LC/MS (m/z) [M+1]+ 450.2 (calculated for C20H23F3N7O2, 450.4).

Workup

temperatureto warm to rt
concentrationthe reaction was concentrated in vacuo
customto afford a yellow oil
customPurification via flash chromatography (inactivated with NH3, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-a02eba7ab2464be8beea810364f5803c
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550474B2

Reaction notes

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