HCID 59410229, compound → HCID 59410230, compound

HRID 1891388Notes

Reaction equation

HRID 1891388 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([C:12]2[CH:13]=[N:14][C:15]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:17]=2[C:18]#[N:19])=[CH:7][C:6]=1[S:24]([N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH3:38])([CH3:37])[CH2:29][CH2:28]1)(=[O:26])=[O:25]>C1COCC1.Cl>[Cl:11][C:9]1[C:8]([C:12]2[CH:13]=[N:14][C:15]([C:20]([F:22])([F:23])[F:21])=[CH:16][C:17]=2[C:18]#[N:19])=[CH:7][C:6]([S:24]([N:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]([CH3:38])([CH3:37])[CH2:29][CH2:28]2)(=[O:25])=[O:26])=[C:5]([CH2:4][C:3]([OH:39])=[O:2])[CH:10]=1

Participants

4

Reactant 1

HCID 59410229HCID 59410229, compound

Product 1

HCID 59410230HCID 59410230, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

[5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-acetic acid methyl ester 16-1 (36.4 mg, 0.06 mmol) was heated in a mixture of THF (2 mL) and 6N HCl (2 mL) for 16 hrs. The mixture was concentrated and extracted with ethyl acetate. The organic layer was separated, dried and purified by a prep. TLC plate eluting with 10% MeOH in DCM to yield 5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-acetic acid 17-1 (27.3 mg). MS: 564.0 (M+H)+; tR=8.96 min (method 2).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. customdried
  5. custompurified by a prep
  6. washTLC plate eluting with 10% MeOH in DCM
  7. customto yield 5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-acetic acid 17-1 (27.3 mg)

Sources & evidence

ORD record
ord-8c9807d2f8b847bda7d0923ec4008000
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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