Hydrochloric Acid → HCID 86298061, compound

HRID 2175757Notes

Reaction equation

HRID 2175757 reaction equation
[O:1]=[C:2]([N:12]1[CH2:17][CH2:16][C:15]2([CH2:26][C:25]3[C:20](=[N:21][CH:22]=[C:23](/[CH:27]=[CH:28]/[C:29](=[O:42])[N:30]4[CH2:35][CH2:34][C:33]([CH2:36][C:37]5[S:38][CH:39]=[CH:40][N:41]=5)=[CH:32][CH2:31]4)[CH:24]=3)[NH:19][C:18]2=[O:43])[CH2:14][CH2:13]1)[CH2:3][NH:4]C(=O)OC(C)(C)C.[ClH:44]>O1CCOCC1.CCOCC>[ClH:44].[NH2:4][CH2:3][C:2]([N:12]1[CH2:13][CH2:14][C:15]2([CH2:26][C:25]3[C:20](=[N:21][CH:22]=[C:23](/[CH:27]=[CH:28]/[C:29](=[O:42])[N:30]4[CH2:35][CH2:34][C:33]([CH2:36][C:37]5[S:38][CH:39]=[CH:40][N:41]=5)=[CH:32][CH2:31]4)[CH:24]=3)[NH:19][C:18]2=[O:43])[CH2:16][CH2:17]1)=[O:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90443307HCID 90443307, compound

Product 1

HCID 86298061HCID 86298061, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of (E)-tert-butyl (2-oxo-2-(2-oxo-6-(3-oxo-3-(4-(thiazol-2-ylmethyl)-5,6-dihydropyridin-1(2H)-yl)prop-1-en-1-yl)-2,4-dihydro-1Hspiro[[1,8]naphthyridine-3,4′-piperidin]-1′-yl)ethyl)carbamate (41.1) (20 mg, 0.03 mmol) in 1,4-dioxane (1 mL) was added 2M HCl in ether (0.24 mL) drop wise at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 3 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 brown solid (20 mg); 1H NMR (400 MHz, DMSO-d6) δ 10.79 (s, 1H), 8.41 (d, J=2.0 Hz, 1H), 8.09 (s, 1H), 8.08-8.00 (m, 3H), 7.71 (d, J=3.4 Hz, 1H), 7.61 (d, J=3.4 Hz, 1H), 7.46 (d, J=15.2 Hz, 1H), 7.28-7.14 (m, 1H), 5.68-5.65 (m, 1H), 4.26-4.18 (m, 1H), 4.08-4.02 (m, 1H), 3.92-3.80 (m, 4H), 3.80-3.72 (m, 3H), 3.68-3.60 (m, 1H), 3.54-3.40 (m, 2H), 2.98 (s, 2H), 2.20-2.04 (m, 2H), 1.92-1.83 (m, 1H), 1.82-1.68 (m, 1H), 1.48-1.32 (m, 2H); ES-MS: 507.3 (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-044e3d393af443cc8cc5debd0680b50a
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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