Trifluoroacetic acid → HCID 178467119, compound

HRID 2178851Notes

Reaction equation

C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]4[CH:30]=[C:29]([F:31])[C:28]([OH:32])=[C:27]([Cl:33])[CH:26]=4)[N:23]=3)[N:18]=[CH:17][C:16]=2[C:34](=[O:36])[CH3:35])[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:57].Cl>>[ClH:33].[ClH:57].[NH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]4[CH:30]=[C:29]([F:31])[C:28]([OH:32])=[C:27]([Cl:33])[CH:26]=4)[N:23]=3)[N:18]=[CH:17][C:16]=2[C:34](=[O:36])[CH3:35])[CH2:10][CH2:9]1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

HCID 137231119HCID 137231119, compound

Product 1

HCID 178467119HCID 178467119, compoundYield 45%

Procedure

Following general procedure IV-2, tert-butyl(4-{[3-acetyl-6-(3-chloro-5-fluoro-4-hydroxyphenyl)-1,5-naphthyridin-4-yl]amino}cyclohexyl)carbamate (0.20 mmol) was reacted with TFA (2 mL) followed by formation of the dihydrochloride salt to afford the desired product (45 mg, 45% over two steps) as a white solid: 1H NMR (500 MHz, D2O) δ 8.99 (s, 1H), 8.13 (d, J=9.0 Hz, 1H), 8.03 (d, J=9.0 Hz, 1H), 7.40-7.34 (m, 2H), 4.91-4.94 (m, 1H), 3.35-3.28 (m, 1H), 2.72 (s, 3H), 2.30-2.22 (m, 2H), 2.21-2.14 (m, 2H), 1.75-1.68 (m, 2H), 1.56-1.48 (m, 2H); ESI MS m/z 429 [M+H]+; HPLC>99% (AUC), tR=9.10 min.

Sources & evidence

ORD record: ord-491dcc34fd294966b13d93091056f69d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067937B2

Reaction notes

Loading…