Trifluoroacetic acid → HCID 178467089, compound

HRID 526132Notes

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]([CH2:21][N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[CH2:17][CH2:16]1)=[N:11][C:10]([C:35]1[CH:40]=[C:39]([Cl:41])[C:38]([OH:42])=[C:37]([Cl:43])[CH:36]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>>[ClH:41].[ClH:41].[ClH:41].[Cl:41][C:39]1[CH:40]=[C:35]([C:10]2[N:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[N:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[C:13]3[NH:14][C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][N:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)[CH2:17][CH2:16]2)[CH:36]=[C:37]([Cl:43])[C:38]=1[OH:42]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 136927323HCID 136927323, compound

Product 1

HCID 178467089HCID 178467089, compoundYield 176.8%

Procedure

Following general procedure IV-2, tert-butyl 4-((4-((3-acetyl-6-(3,5-dichloro-4-hydroxy-phenyl)-1,5-naphthyridin-4-yl)amino)cyclohexyl)methyl)piperazine-1-carboxylate (0.298 mmol) was reacted with TFA (2 mL) followed by formation of the trihydrochloride salt to afford the desired product (84 mg, 47% over two steps) as a yellow solid: 1H NMR (500 MHz, D2O) δ 9.00 (s, 1H), 8.22-8.11 (m, 2H), 7.59 (s, 2H), 5.06 (m, 1H), 4.76-4.71 (m, 1H), 4.66 (s, 1H), 3.60 (s, 8H), 3.15 (d, J=6.7 Hz, 2H), 2.74 (s, 3H), 2.25-2.23 (m, 2H), 2.02-1.97 (m, 2H), 1.60-1.58 (m, 2H), 1.24-1.20 (m, 2H); ESI MS m/z 528 [M+H]+; HPLC 98.0% (AUC), tR=9.29 min.

Sources & evidence

ORD record: ord-632f082744b5498ab94d0a6a880b9426
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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