Trifluoroacetic acid → HCID 178467096, compound

HRID 526128Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH:15]1[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]1)=[N:11][C:10]([C:29]1[CH:34]=[C:33]([Cl:35])[C:32]([OH:36])=[C:31]([Cl:37])[CH:30]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:57].Cl>>[ClH:35].[ClH:57].[NH2:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([NH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:29]4[CH:30]=[C:31]([Cl:37])[C:32]([OH:36])=[C:33]([Cl:35])[CH:34]=4)[N:11]=3)[N:6]=[CH:5][C:4]=2[C:1](=[O:3])[CH3:2])[CH2:16][CH2:17]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-8c86967e6a964866aa12d43e17fb7ae5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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