HCID 89739155, compound → HCID 71678378, compound

HRID 2278407Notes

Reaction equation

HRID 2278407 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][C:23]([C:25]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[C:30]5[C:26]=4[CH:27]=[CH:28][NH:29]5)=[N:22][C:21]=3[C:38](=[O:40])[NH2:39])=[CH:16][CH:15]=2)[CH2:10][C:9]1([CH3:42])[CH3:41])=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:36][C:34]([F:35])([F:37])[C:31]1[CH:32]=[CH:33][C:25]([C:23]2[O:24][C:20]([C:17]3[CH:16]=[CH:15][C:14]([N:11]4[CH2:12][CH2:13][NH:8][C:9]([CH3:41])([CH3:42])[CH2:10]4)=[CH:19][CH:18]=3)=[C:21]([C:38]([NH2:39])=[O:40])[N:22]=2)=[C:26]2[C:30]=1[NH:29][CH:28]=[CH:27]2

Participants

4

Reactant 1

HCID 89739155HCID 89739155, compound

Product 1

HCID 71678378HCID 71678378, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-{4-[4-Carbamoyl-2-(7-trifluoromethyl-1H-indol-4-yl)-oxazol-5-yl]-phenyl}-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (0.18 g crude) was dissolved in a mixture of DCM and TFA (30 mL 2:1), and the solution was stirred at RT for 2 hrs, when the solvent was removed in vacuo. The residue was partitioned between water and EtOAc. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo to give the crude product which was purified by prep-HPLC to give the title compound (60 mg, 41% from ethyl 5-(4-(4-(tert-butoxycarbonyl)-3,3-dimethylpiperazin-1-yl)phenyl)-2-iodooxazole-4-carboxylate).

Workup

  1. customwhen the solvent was removed in vacuo
  2. customThe residue was partitioned between water and EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent was removed in vacuo
  5. customto give the crude product which
  6. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-b6a97485779b4e6481627fad5c9b310b
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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