HCID 67463891, compound → HCID 67459150, compound

HRID 554858Notes

Reaction equation

HRID 554858 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:24]=[CH:23][C:22]4[N:25]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=5)[S:27][C:21]=4[C:20]3=[O:38])=[CH:15][C:14]=2[O:39][CH3:40])[CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:24]=[CH:23][C:22]4[N:25]=[C:26]([C:28]5[CH:29]=[CH:30][C:31]([C:34]([F:35])([F:37])[F:36])=[CH:32][CH:33]=5)[S:27][C:21]=4[C:20]3=[O:38])=[CH:15][C:14]=2[O:39][CH3:40])[CH2:9]1

Participants

4

Reactant 1

HCID 67463891HCID 67463891, compound

Product 1

HCID 67459150HCID 67459150, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve 3-{2-methoxy-4-[4-oxo-2-(4-trifluoromethyl-phenyl)-4H-thiazolo[5,4-c]pyridin-5-yl]-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester (1.3 g, 2.27 mmol) in dichloromethane (12 mL) and slowly add trifluoroacetic acid (6 mL). Stir the mixture for one hour and then evaporate. Apply the residue to a 10 g SCX column with dichloromethane. Wash the column with methanol then elute the material using 1:1 dichloromethane:2N ammonia/methanol. Concentrate to give 0.909 g (85%) of the desired product as a white solid. MS/ES m/z 474.0 [M+1]+.

Workup

  1. customevaporate
  2. washWash the column with methanol
  3. washthen elute the material
  4. concentrationConcentrate

Sources & evidence

ORD record
ord-084fd6ef238d46c4b72ecc38d98a82f6
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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