Trifluoroacetic acid → 4'-Fluoro-biphenyl-4-carboxylic acid [2-(methyl-pyrrolidin-3-ylmethyl-amino)-benzothiazol-6-yl]-amide

HRID 1174957Notes

Reaction equation

HRID 1174957 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][N:14]([C:16]2[S:17][C:18]3[CH:24]=[C:23]([NH:25][C:26]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=5)=[CH:30][CH:29]=4)=[O:27])[CH:22]=[CH:21][C:19]=3[N:20]=2)[CH3:15])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:15][N:14]([CH2:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[C:16]1[S:17][C:18]2[CH:24]=[C:23]([NH:25][C:26]([C:28]3[CH:29]=[CH:30][C:31]([C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)=[CH:32][CH:33]=3)=[O:27])[CH:22]=[CH:21][C:19]=2[N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57771739HCID 57771739, compound

Product 1

HCID 577717144'-Fluoro-biphenyl-4-carboxylic acid [2-(methyl-pyrrolidin-3-ylmethyl-amino)-benzothiazol-6-yl]-amideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Place 3-[({6-{(4′-fluoro-biphenyl-4-carbonyl)-amino]-benzothiazol-2-yl}-methyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester in DCM (50 mL). Add trifluoroacetic acid (100 mL) and stir at rt for 6 h. Concentrate in vacuo and then add DCM:Hexane and concentrate in vacuo. Dissolve the residue in 1:1 MeOH:DCM and add polyvinyl pyridine (3 g) and stir for 15 min. Filter the solution and wash the resin with DCM. Collect the filtrate and concentrate in vacuo to yield 1.50 g (95%) of the title compound. mass spectrum (ion-spray): (m/z)=461.0 (M+1).

Workup

  1. concentrationConcentrate in vacuo
  2. concentrationadd DCM:Hexane and concentrate in vacuo
  3. dissolutionDissolve the residue in 1:1 MeOH
  4. additionDCM and add polyvinyl pyridine (3 g)
  5. filtrationFilter the solution
  6. washwash the resin with DCM
  7. customCollect the filtrate
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-a27b7fb14aed42bfbdfbc76ece05878c
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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