Water → HCID 59156758, compound

HRID 2390844Notes

Reaction equation

HRID 2390844 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[C:17](/[CH:25]=[CH:26]/[C:27]3[CH:35]=[CH:34][C:33]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:32][C:28]=3[C:29]([OH:31])=[O:30])[CH:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[C:17]([CH:25]3[CH2:26][C:27]4[C:28](=[CH:32][C:33]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:34][CH:35]=4)[C:29](=[O:31])[O:30]3)[CH:18]=[C:19]([C:21]([CH3:23])([CH3:22])[CH3:24])[CH:20]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 68574130HCID 68574130, compound

Product 1

HCID 59156758HCID 59156758, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

step b—A solution of 199a, TFA (3 mL), H2O (1 mL) and DCM (10 mL) was heated at reflux for 3 h, cooled and diluted with a ice-water mixture. The pH of the solution was adjusted to ca. 3 with sat'd. NaHCO3 and extracted with EtOAc. The combined extracts were washed with brine, dried, filtered and evaporated to afford N-{3-[3-(2-benzyloxy-pyridin-3-yl)-5-tert-butyl-phenyl]-1-oxo-isochroman-7-yl}-methanesulfonamide (199b)

Workup

  1. temperatureat reflux for 3 h
  2. temperaturecooled
  3. extractionNaHCO3 and extracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9534c0c65cfb4291be3a84dab9acd11e
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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