Trifluoroacetic acid → (E)-6-(3-oxo-3-(4-(thiazol-2-ylmethyl)-5,6-dihydropyridin-1(2H)-yl)prop-1-en-1-yl)-1H-spiro[[1,8]naph-thyridine-3,4'-piperidin]-2(4H)-one 2,2,2-trifluoroacetate

HRID 2175753Notes

Reaction equation

HRID 2175753 reaction equation
[O:1]=[C:2]1[C:11]2([CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH2:10][C:9]2[C:4](=[N:5][CH:6]=[C:7](/[CH:24]=[CH:25]/[C:26](=[O:39])[N:27]3[CH2:32][CH2:31][C:30]([CH2:33][C:34]4[S:35][CH:36]=[CH:37][N:38]=4)=[CH:29][CH2:28]3)[CH:8]=2)[NH:3]1.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>C(Cl)Cl>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[O:39]=[C:26]([N:27]1[CH2:32][CH2:31][C:30]([CH2:33][C:34]2[S:35][CH:36]=[CH:37][N:38]=2)=[CH:29][CH2:28]1)/[CH:25]=[CH:24]/[C:7]1[CH:8]=[C:9]2[C:4](=[N:5][CH:6]=1)[NH:3][C:2](=[O:1])[C:11]1([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[CH2:10]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86296668(E)-tert-butyl 2-oxo-6-(3-oxo-3-(4-(thiazol-2-ylmethyl)-5,6-dihydropyridin-1(2H)-yl)prop-1-en-1-yl)-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4'-piperidine]-1'-carboxylate2×

Product 1

HCID 86297851(E)-6-(3-oxo-3-(4-(thiazol-2-ylmethyl)-5,6-dihydropyridin-1(2H)-yl)prop-1-en-1-yl)-1H-spiro[[1,8]naph-thyridine-3,4'-piperidin]-2(4H)-one 2,2,2-trifluoroacetateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of (E)-tert-butyl 2-oxo-6-(3-oxo-3-(4-(thiazol-2-ylmethyl)-5,6-dihydropyridin-1(2H)-yl)prop-1-en-1-yl)-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-1′-carboxylate (Compound 1) (0.6 g, 1.52 mmol) in CH2Cl2 (15 mL) was added trifluoro acetic acid (0.58 mL, 7.61 mmol) at 20-35° C. and the reaction mixture was allowed to stir at 20-35° C. for 4 h. Then the reaction mixture was rotary evaporated under vacuum to get residue which was triturated with diethyl ether to get the desired compound as a yellow solid (500 mg, 82%); 1H NMR (400 MHz, DMSO-d6) δ 10.88 (s, 1H), 8.50-8.32 (m, 3H), 8.07 (s, 1H), 7.71 (d, J=3.4 Hz, 1H), 7.61 (d, J=3.4 Hz, 1H), 7.46 (d, J=15.7 Hz, 1H), 7.28-7.14 (m, 1H), 5.68-5.65 (m, 1H), 4.26-4.20 (m, 1H), 4.08-4.02 (m, 1H), 3.78-3.72 (m, 3H), 3.68-3.62 (m, 1H), 3.16-3.06 (m, 4H), 2.97 (s, 2H), 2.20-2.04 (m, 2H), 2.03-1.92 (m, 2H), 1.62-1.48 (m, 2H); ES-MS: 450.2 (M+1)+.

Workup

  1. customThen the reaction mixture was rotary evaporated under vacuum
  2. customto get residue which
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-85bcfc81297943658dfe20f29b6e049f
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

Loading…