Triethylamine → (E)-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'-carboxamide

HRID 2175756Notes

Reaction equation

HRID 2175756 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]([N:28]1[CH2:33][CH2:32][C:31]([CH2:34][C:35]2[S:36][CH:37]=[CH:38][N:39]=2)=[CH:30][CH2:29]1)/[CH:10]=[CH:11]/[C:12]1[CH:13]=[C:14]2[C:24](=[N:25][CH:26]=1)[NH:23][C:22](=[O:27])[C:16]1([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH2:15]2.C(N(CC)CC)C.[C:47](=O)([O:49]C1C=CC=CC=1)[NH2:48]>CS(C)=O>[O:27]=[C:22]1[C:16]2([CH2:21][CH2:20][N:19]([C:47]([NH2:48])=[O:49])[CH2:18][CH2:17]2)[CH2:15][C:14]2[C:24](=[N:25][CH:26]=[C:12](/[CH:11]=[CH:10]/[C:9](=[O:8])[N:28]3[CH2:33][CH2:32][C:31]([CH2:34][C:35]4[S:36][CH:37]=[CH:38][N:39]=4)=[CH:30][CH2:29]3)[CH:13]=2)[NH:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69322Phenyl carbamateHCID 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-trifluoroacetate2×

Product 1

HCID 86298059(E)-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'-carboxamideYield 31.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of (E)-6-(3-oxo-3-(4-(thiazol-2-ylmethyl)-5,6-dihydro pyridin-1(2H)-yl)prop-1-en-1-yl)-1H-spiro[[1,8]naph-thyridine-3,4′-piperidin]-2(4H)-one 2,2,2-trifluoroacetate (Compound 34) (150 mg, 0.26 mmol) in DMSO (2 mL) were added triethylamine (110 mg, 1.04 mmol) and phenyl carbamate (44 mg, 0.32 mmol) at 20-35° C. and the reaction mixture was allowed to stir at 20-35° C. for 16 h. Then the reaction mixture was poured into ice water (50 mL), obtained solid was filtered, washed with water and dried under vacuum to get the desired compound as a yellow solid (40 mg, 31%); 1H NMR (400 MHz, DMSO-d6) δ 10.71 (s, 1H), 8.37 (d, J=2.0 Hz, 1H), 8.10 (s, 1H), 7.71 (d, J=3.4 Hz, 1H), 7.61 (d, J=3.4 Hz, 1H), 7.45 (d, J=15.2 Hz, 1H), 7.28-7.14 (m, 1H), 5.93 (s, 2H), 5.68-5.65 (m, 1H), 4.28-4.20 (m, 1H), 4.08-4.02 (m, 1H), 3.76-3.72 (m, 3H), 3.66-3.62 (m, 1H), 3.60-3.52 (m, 2H), 3.18 (t, J=10.0 Hz, 2H), 2.95 (s, 2H), 2.20-2.06 (m, 2H), 1.76-1.66 (m, 2H), 1.34-1.24 (m, 2H); ES-MS: 493.3 (M+1)+.

Workup

  1. customobtained solid
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-cde291be428f47fdba6eae5e506d076e
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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