Trifluoroacetic acid → HCID 15952366, compound

HRID 2244255Notes

Reaction equation

HRID 2244255 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[N:20]3[C:14]([CH2:15][N:16]([C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]5[C:34]([C:39]([O:41]C(C)(C)C)=[O:40])=[CH:35][CH:36]=[CH:37][CH:38]=5)=[CH:29][CH:28]=4)=[O:26])[C:17]4[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=4[CH2:19]3)=[CH:13][CH:12]=2)=[O:10])[CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[N:20]3[C:14]([CH2:15][N:16]([C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]5[C:34]([C:39]([OH:41])=[O:40])=[CH:35][CH:36]=[CH:37][CH:38]=5)=[CH:29][CH:28]=4)=[O:26])[C:17]4[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=4[CH2:19]3)=[CH:13][CH:12]=2)=[O:10])[CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68687808HCID 68687808, compound

Product 1

HCID 15952366HCID 15952366, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4′-{[3-{[(pyridin-3-ylmethyl)amino]carbonyl}-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl]carbonyl}-1,1′-biphenyl-2-carboxylate of Example 64 (0.710 g, 1.186 mmol) in dry dichloromethane (10 mL) was added trifluoroacetic acid (10 mL) and the reaction mixture stirred at room temperature under nitrogen for 1.75 hours. The reaction mixture was then concentrated in vacuo and the resulting solid dissolved in ethyl acetate (50 mL). The organic phase was extracted with 2 M sodium hydroxide (2×50 mL) and the combined aqueous extracts acidified to pH 1 by the addition of concentrated hydrochloric acid. The resulting white suspension was cooled to 4° C. for 1 hour, the solid product filtered, washed with water and then dried in vacuo at 50° C. overnight to afford the title compound (0.345 g, 54%) as a white solid, m.p. 189-191° C.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe resulting solid dissolved in ethyl acetate (50 mL)
  3. extractionThe organic phase was extracted with 2 M sodium hydroxide (2×50 mL)
  4. additionthe combined aqueous extracts acidified to pH 1 by the addition of concentrated hydrochloric acid
  5. temperatureThe resulting white suspension was cooled to 4° C. for 1 hour
  6. filtrationthe solid product filtered
  7. washwashed with water
  8. customdried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-f03555dea9f24fbf9042c85b6de7573a
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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