Trifluoroacetic acid → 2-[(2R)-2-(Hydroxymethyl)morpholin-4-yl]-5-({1-[4-(1-methylethenyl)-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-1,3-thiazol-4(5H)-one

HRID 2384851Notes

Reaction equation

HRID 2384851 reaction equation
O[C:2]([C:5]1[CH:35]=[CH:34][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH:19]=[C:20]4[S:24][C:23]([N:25]5[CH2:30][CH2:29][O:28][CH:27]([CH2:31][OH:32])[CH2:26]5)=[N:22][C:21]4=[O:33])=[CH:16][CH:17]=3)[CH:12]=[N:11]2)=[C:7]([C:36]([F:39])([F:38])[F:37])[CH:6]=1)([CH3:4])[CH3:3].C(O)(C(F)(F)F)=O>ClCCl>[OH:32][CH2:31][C@@H:27]1[O:28][CH2:29][CH2:30][N:25]([C:23]2[S:24][C:20](=[CH:19][C:15]3[CH:14]=[C:13]4[C:18](=[CH:17][CH:16]=3)[N:10]([CH2:9][C:8]3[CH:34]=[CH:35][C:5]([C:2]([CH3:4])=[CH2:3])=[CH:6][C:7]=3[C:36]([F:37])([F:39])[F:38])[N:11]=[CH:12]4)[C:21](=[O:33])[N:22]=2)[CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672408885-{1-[4-(1-Hydroxy-1-methyl-ethyl)-2-trifluoromethyl-benzyl]-1H-indazol-5-ylmethylene}-2-(2-hydroxymethyl-morpholin-4-yl)-thiazol-4-one

Product 1

HCID 672404252-[(2R)-2-(Hydroxymethyl)morpholin-4-yl]-5-({1-[4-(1-methylethenyl)-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-1,3-thiazol-4(5H)-oneYield 24.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-{1-[4-(1-Hydroxy-1-methyl-ethyl)-2-trifluoromethyl-benzyl]-1H-indazol-5-ylmethylene}-2-(2-hydroxymethyl-morpholin-4-yl)-thiazol-4-one (400 mg, 0.71 mmol) in dichloromethane (2 mL) was treated with TFA (2 mL). The reaction mixture was stirred at room temperature for 1.5 hour and partitioned between water and dichloromethane. The dichloromethane layer was washed with aqueous saturated sodium carbonate, brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified via flash chromatography (90% ethyl acetate in Heptane) to yield the title compound as a solid (94 mg, 24% yield).

Workup

  1. custompartitioned between water and dichloromethane
  2. washThe dichloromethane layer was washed with aqueous saturated sodium carbonate, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude solid
  7. customThe crude solid was purified via flash chromatography (90% ethyl acetate in Heptane)

Sources & evidence

ORD record
ord-76ad8f1ec802451abe3bc0e631321d21
Source dataset
uspto-grants-2012_09
Patent number
US08263781B2

Reaction notes

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