Acetic Acid → 17-[2-(6-Methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yl-oxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid

HRID 1692473Notes

Reaction equation

HRID 1692473 reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]12[CH2:25][CH:24]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH3:26])[C:16](=[O:27])[CH:15]1[CH:11]([CH2:12][CH:13]([O:28][C:29]3[C:38]4[C:33](=[C:34]([CH3:41])[C:35]([O:39][CH3:40])=[CH:36][CH:37]=4)[N:32]=[C:31]([C:42]4[CH:47]=[CH:46][CH:45]=[C:44]([CH3:48])[N:43]=4)[CH:30]=3)[CH2:14]1)[C:10](=[O:49])[NH:9]2)=[O:7])C.CO.C(O)(=O)C>C1COCC1.O>[CH3:48][C:44]1[N:43]=[C:42]([C:31]2[CH:30]=[C:29]([O:28][CH:13]3[CH2:12][CH:11]4[CH:15]([C:16](=[O:27])[N:17]([CH3:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH:23][CH:24]5[C:8]([C:6]([OH:7])=[O:5])([NH:9][C:10]4=[O:49])[CH2:25]5)[CH2:14]3)[C:38]3[C:33](=[C:34]([CH3:41])[C:35]([O:39][CH3:40])=[CH:36][CH:37]=3)[N:32]=2)[CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 6687158517-[2-(6-Methylpyridin-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo-[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester

Product 1

HCID 7667481117-[2-(6-Methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yl-oxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acidYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (0.42 mL, 1M) was added to a solution of 17-[2-(6-methylpyridin-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo-[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester (101, 27 mg, 0.042 mmol) in a mixture of THF:MeOH:H2O, 2:1:1 (6 mL). The resulting solution was stirred at room temperature overnight, then the pH was adjusted to 6 with acetic acid. The reaction mixture was successively diluted with water, extracted with CH2Cl2, dried (MgSO4), filtered and evaporated to give 17 mg (65%) of the title compound: m/z=613 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-c73b404331b3414c9adce282d921a376
Source dataset
uspto-grants-2012_04
Patent number
US08153800B2

Reaction notes

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