Trifluoroacetic acid → HCID 178467096, compound

HRID 2178850Notes

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]([Cl: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:31].[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:26]=[C:27]([Cl:33])[C:28]([OH:32])=[C:29]([Cl:31])[CH:30]=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 136981866HCID 136981866, compound

Product 1

HCID 178467096HCID 178467096, compoundYield 27%

Procedure

Following general procedure IV-2, tert-butyl(4-{[3-acetyl-6-(3,5-dichloro-4-hydroxyphenyl)-1,5-naphthyridin-4-yl]amino}cyclohexyl)carbamate (0.23 mmol) was reacted with TFA (2 mL) followed by formation of the dihydrochloride salt to afford the desired product (32 mg, 27% over two steps) as a gray solid: 1H NMR (300 MHz, D2O) δ 8.96 (s, 1H), 8.18-8.00 (m, 2H), 7.53 (s, 2H), 3.28-3.23 (m, 1H), 2.68 (s, 3H), 2.28-2.24 (m, 2H), 2.16-2.13 (m, 2H), 1.76-1.64 (m, 2H), 1.57-1.45 (m, 2H); ESI MS m/z 445 [M+H]+; HPLC 98.4% (AUC), tR=9.34 min.

Sources & evidence

ORD record: ord-afb145beb535431abfc7325c1112ca97
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067937B2

Reaction notes

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