Trifluoroacetic acid → 1-[[4-[8-Chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]pyrrolidine-2-carbonyl]amino]-2-vinylcyclopropanecarboxylic acid ethyl ester

HRID 1669569Notes

Reaction equation

HRID 1669569 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14]2[C:23]3[C:18](=[C:19]([Cl:26])[C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[N:17]=[C:16]([C:27]3[S:28][CH:29]=[C:30]([CH:32]([CH3:34])[CH3:33])[N:31]=3)[CH:15]=2)[CH2:10][CH:9]1[C:35](=[O:47])[NH:36][C:37]1([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:39][CH:38]1[CH:40]=[CH2:41])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:45]([O:44][C:42]([C:37]1([NH:36][C:35]([CH:9]2[CH2:10][CH:11]([O:13][C:14]3[C:23]4[C:18](=[C:19]([Cl:26])[C:20]([O:24][CH3:25])=[CH:21][CH:22]=4)[N:17]=[C:16]([C:27]4[S:28][CH:29]=[C:30]([CH:32]([CH3:33])[CH3:34])[N:31]=4)[CH:15]=3)[CH2:12][NH:8]2)=[O:47])[CH2:39][CH:38]1[CH:40]=[CH2:41])=[O:43])[CH3:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673198764-[8-Chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2-(1-ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673186401-[[4-[8-Chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]pyrrolidine-2-carbonyl]amino]-2-vinylcyclopropanecarboxylic acid ethyl esterYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-[8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2-(1-ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester (49, 0.7 g, 1.02 mmol) in CH2Cl2 (8 mL) was added trifluoroacetic acid (2.0 mL). After 2 h at room temperature, the reaction mixture was concentrated and the residue was partitioned between a saturated solution of NaHCO3 and DCM. The organic layer was dried (MgSO4) filtered and concentrated to give 580 mg (97%) of the title product (50) as a colorless oil: m/z=585 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was partitioned between a saturated solution of NaHCO3 and DCM
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-42871b37770a42b88b6fb7a9a73a95aa
Source dataset
uspto-grants-2011_08
Patent number
US07989471B2

Reaction notes

Loading…