Hydrochloric Acid → HCID 59415795, compound

HRID 2061836Notes

Reaction equation

HRID 2061836 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([N:14]2[C:23]3[C:18](=[CH:19][C:20]([C:24]4[CH:25]=[N:26][C:27]([NH:39][C:40]([NH:42][CH2:43][CH3:44])=[O:41])=[CH:28][C:29]=4[C:30]4[S:31][CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[N:34]=4)=[CH:21][CH:22]=3)[C:17](=[O:45])[C:16]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:15]2)[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>ClCCl.CO.O>[CH2:43]([NH:42][C:40](=[O:41])[NH:39][C:27]1[N:26]=[CH:25][C:24]([C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[N:14]([C@H:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:15]=[C:16]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[C:17]3=[O:45])=[C:29]([C:30]2[S:31][CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[N:34]=2)[CH:28]=1)[CH3:44]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 59416115HCID 59416115, compound

Product 1

HCID 59415795HCID 59415795, compoundYield 72.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-ethyl 1-(1-(tert-butoxycarbonyl)piperidin-3-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydroquinoline -3-carboxylate (Example 259, 5.00 g, 7.00 mmol) was taken up in dichloromethane (10 mL) and 4M HCl in dioxane (0.486 mL, 13.99 mmol) was added while stirring at RT for 1 h. Removed solvent in vaccuo and residue was taken back up in methanol and water. The reaction was neutralized using NaHCO3 and a precipitate was collected, washed with ether and dried under high vacuum overnight to give (S)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1-(piperidin-3-yl)-1,4-dihydroquinoline-3-carboxylate (3.10 g, 72.1%).

Workup

  1. customa precipitate was collected
  2. washwashed with ether
  3. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-e6569cb1197440f9b14c028c37517709
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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