(4'-{4-[4-(Propane-1-sulfonyl)-piperazin-1-ylmethyl]-phenylcarbamoyl}-6-trifluoromethoxy-biphenyl-3-yl)-carbamic acid tert-butyl ester → 5'-Amino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid {4-[4-(propane-1-sulfonyl)-piperazin-1-ylmethyl]-phenyl}-amide

HRID 1678498Notes

Reaction equation

HRID 1678498 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[C:10]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:46])[NH:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][N:34]4[CH2:39][CH2:38][N:37]([S:40]([CH2:43][CH2:44][CH3:45])(=[O:42])=[O:41])[CH2:36][CH2:35]4)=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)[C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:12][CH:13]=1)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:43]([S:40]([N:37]1[CH2:38][CH2:39][N:34]([CH2:33][C:30]2[CH:31]=[CH:32][C:27]([NH:26][C:25]([C:22]3[CH:23]=[CH:24][C:19]([C:10]4[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][C:11]=4[O:14][C:15]([F:17])([F:18])[F:16])=[CH:20][CH:21]=3)=[O:46])=[CH:28][CH:29]=2)[CH2:35][CH2:36]1)(=[O:41])=[O:42])[CH2:44][CH3:45]

Participants

4

Reactant 1

HCID 59822362(4'-{4-[4-(Propane-1-sulfonyl)-piperazin-1-ylmethyl]-phenylcarbamoyl}-6-trifluoromethoxy-biphenyl-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 598223685'-Amino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid {4-[4-(propane-1-sulfonyl)-piperazin-1-ylmethyl]-phenyl}-amideYield 95.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(4′-{4-[4-(propane-1-sulfonyl)-piperazin-1-ylmethyl]-phenylcarbamoyl}-6-trifluoromethoxy-biphenyl-3-yl)-carbamic acid tert-butyl ester (459 mg) in DCM (4 ml) and Trifluoroacetic Acid (4 ml) was stirred for 2 hrs. The mixture was evaporated and the residue partitioned between EtOAc and saturated potassium carbonate. The dried extracts were then evaporated giving the title compound as a tan foam (374 mg).

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between EtOAc and saturated potassium carbonate
  3. customThe dried extracts were then evaporated

Sources & evidence

ORD record
ord-43a8d680716a4560b69edaee6e5e357c
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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