p-Toluenesulfonic acid monohydrate → HCID 86603842, compound

HRID 226496Notes

Reaction equation

HRID 226496 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:22]=[CH:23]/[C:24]([NH:26][O:27]C2CCCCO2)=[O:25])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10]1.O.[CH3:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([OH:45])(=[O:44])=[O:43])=[CH:38][CH:37]=1>CO>[CH3:35][C:36]1[CH:37]=[CH:38][C:39]([S:42]([OH:45])(=[O:44])=[O:43])=[CH:40][CH:41]=1.[CH3:35][C:36]1[CH:37]=[CH:38][C:39]([S:42]([OH:45])(=[O:44])=[O:43])=[CH:40][CH:41]=1.[F:1][C:2]1[CH:3]=[C:4](/[CH:22]=[CH:23]/[C:24]([NH:26][OH:27])=[O:25])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86603844HCID 86603844, compound

Product 1

HCID 86603842HCID 86603842, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2E)-3-(5-fluoro-6-{[(3R)-1-(2-octyn-1-yl)-3-pyrrolidinyl]amino}-3-pyridinyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (155 mg) in methanol (3.5 ml) was added 4-methylbenzenesulfonic acid hydrate (122 mg) at 25° C. and then stirred at the same temperature for 1 hour. The mixture was concentrated under reduced pressure. The resulting residue was triturated with a mixed solvent of ethyl acetate, diisopropyl ether and methanol. Title compound (178 mg, 73%) was obtained as colorless powder.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe resulting residue was triturated with a mixed solvent of ethyl acetate, diisopropyl ether and methanol

Sources & evidence

ORD record
ord-86c081e4e5124d2390cecca5fe0c326d
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

Loading…