Trifluoroacetic acid → HCID 178522005, compound

HRID 1521760Notes

Reaction equation

HRID 1521760 reaction equation
[O:1]=[C:2]1[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]5[N:26]=[CH:27][N:28](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[CH:29]=5)[CH:20]=4)=[O:17])=[CH:12][C:11]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:28]1[CH:29]=[C:25]([C:21]2[CH:20]=[C:19]([NH:18][C:16]([C:13]3[CH:14]=[CH:15][C:10]4[N:9]=[C:8]5[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][N:7]5[C:11]=4[CH:12]=3)=[O:17])[CH:24]=[CH:23][CH:22]=2)[N:26]=[CH:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672378591-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxamide

Product 1

HCID 178522005HCID 178522005, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxamide (53 mg, 0.08 mmol) in CH2Cl2 (3 mL) is added TFA (0.5 mL) and the solution is stirred for 2 h at room temperature. The solvent is evaporated and the residue treated with 0.1M aqueous NaOH solution. A brown solid is formed which is collected by filtration, washed with CH2Cl2, and dried to afford the title compound (26 mg, 80%).

Workup

  1. customThe solvent is evaporated
  2. additionthe residue treated with 0.1M aqueous NaOH solution
  3. customA brown solid is formed which
  4. filtrationis collected by filtration
  5. washwashed with CH2Cl2
  6. customdried

Sources & evidence

ORD record
ord-32fc5a2b0c704b2797ec53ef0008a54b
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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