Trifluoroacetic acid → HCID 66871011, compound

HRID 1692479Notes

Reaction equation

HRID 1692479 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13]([CH:15]1[CH2:19][CH:18]([O:20][C:21]2[C:30]3[C:25](=[C:26]([CH3:33])[C:27]([O:31][CH3:32])=[CH:28][CH:29]=3)[N:24]=[C:23]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]([CH3:42])[CH3:41])[N:35]=3)[CH:22]=2)[CH2:17][CH:16]1[C:43](=[O:55])[NH:44][C:45]1([C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH2:47][CH:46]1[CH:48]=[CH2:49])=[O:14])(C)(C)C.C([SiH](CC)CC)C>C(Cl)Cl>[CH2:53]([O:52][C:50]([C:45]1([NH:44][C:43]([CH:16]2[CH2:17][CH:18]([O:20][C:21]3[C:30]4[C:25](=[C:26]([CH3:33])[C:27]([O:31][CH3:32])=[CH:28][CH:29]=4)[N:24]=[C:23]([C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]([CH3:42])[CH3:41])[N:35]=4)[CH:22]=3)[CH2:19][CH:15]2[C:13]([OH:14])=[O:12])=[O:55])[CH2:47][CH:46]1[CH:48]=[CH2:49])=[O:51])[CH3:54]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66870816HCID 66870816, compound

Product 1

HCID 66871011HCID 66871011, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5 mL) was added at room temperature to a solution of 2-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-[2-(6-isopropyl-pyridin-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-cyclopentanecarboxylic acid tert-butyl ester (109, 590 mg, 0.90 mmol) and triethylsilane (280 mg, 2.5 eq) in CH2Cl2 (5 mL). After 2 h, the reaction mixture was concentrated under reduced pressure to afford the desired product 110, which was used in the next step without further purifications.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-30cb9723dd0a489a8d3dbd2183014e18
Source dataset
uspto-grants-2012_04
Patent number
US08153800B2

Reaction notes

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