Ethyl Acetate → (2R,4S)-4-[(3-Cyano-5-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid carboxymethyl ester

HRID 661462Notes

Reaction equation

HRID 661462 reaction equation
C([O:5][C:6]([CH2:8][O:9][C:10]([N:12]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:19][CH:20]=2)[C@@H:15]([N:26]([CH2:39][C:40]2[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[C:42]([C:50]#[N:51])[CH:41]=2)[C:27]2[N:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:29][N:28]=2)[CH2:14][C@H:13]1[CH2:52][CH3:53])=[O:11])=[O:7])(C)(C)C.C(=O)([O-])O.[Na+].C(OCC)(=O)C>Cl.O1CCOCC1>[C:6]([CH2:8][O:9][C:10]([N:12]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:19][CH:20]=2)[C@@H:15]([N:26]([CH2:39][C:40]2[CH:45]=[C:44]([C:46]([F:47])([F:48])[F:49])[CH:43]=[C:42]([C:50]#[N:51])[CH:41]=2)[C:27]2[N:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:29][N:28]=2)[CH2:14][C@H:13]1[CH2:52][CH3:53])=[O:11])([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86636546(2R,4S)-4-[(3-Cyano-5-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butoxycarbonylmethyl ester

Product 1

HCID 17747006(2R,4S)-4-[(3-Cyano-5-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid carboxymethyl ester

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

The compound obtained in Example 22 above (37 mg) was dissolved in 4N HCl/dioxane (2 ml) and stirred at room temperature for 6.5 hours. A saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added to the reaction mixture and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; chloroform:methanol=1:0→17:3) to give the titled compound (26 mg). MS (m/z): 693 [M+H]+.

Workup

  1. customthe organic layer was separated
  2. washwashed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (silica gel; chloroform:methanol=1:0→17:3)

Sources & evidence

ORD record
ord-d23ccb44a6c1404791838f3de3b60f57
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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