Trifluoroacetic acid → HCID 68510963, compound

HRID 1410206Notes

Reaction equation

HRID 1410206 reaction equation
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[CH:44]=[CH:43][C:21]3[N:22]([CH3:42])[C:23]([NH:25][C:26]4[CH:27]=[C:28]([CH:38]=[CH:39][C:40]=4[Cl:41])[CH2:29][NH:30]C(=O)OC(C)(C)C)=[N:24][C:20]=3[CH:19]=2)=[O:17])=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:30][CH2:29][C:28]1[CH:38]=[CH:39][C:40]([Cl:41])=[C:26]([NH:25][C:23]2[N:22]([CH3:42])[C:21]3[CH:43]=[CH:44][C:18]([C:16]([NH:15][C:12]4[CH:11]=[CH:10][C:9]([Br:8])=[CH:14][CH:13]=4)=[O:17])=[CH:19][C:20]=3[N:24]=2)[CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 46909321HCID 46909321, compound

Product 1

HCID 68510963HCID 68510963, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TFA (1.5 mL) was added to tert-butyl 3-[5-(4-bromophenylcarbamoyl)-1-methyl-2-benzimidazolylamino]-4-chlorobenzylcarbamate (960 mg. 1.7 mmol prepared in analogy to the experimental procedures described above) in DCM (20 mL) at rt. After 16 h at rt TFA (2 mL) was added and the mixture was stirred at rt for 16 h, diluted with DCM and washed with NaHCO3 (aq, sat) and brine, dried and concentrated to give the sub-title compound which was used in the next step without further purification. Yield: 706 mg (90%)

Workup

  1. custom1.7 mmol prepared in analogy to the experimental procedures
  2. customat rt
  3. washwashed with NaHCO3 (aq, sat) and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-427e30d3d2ed4b97bcba43b385e4e0af
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

Loading…