Trifluoroacetic acid → HCID 69310772, compound

HRID 2219665Notes

Reaction equation

HRID 2219665 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([NH:14][C:15](=[O:38])[CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]([C:28](=[O:36])[C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:18]=2[CH3:37])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:11]1([NH:14][C:15](=[O:38])[CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]([C:28](=[O:36])[C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:18]=2[CH3:37])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69316318HCID 69316318, compound

Product 1

HCID 69310772HCID 69310772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.300 g (0.57 mmol) of N-(4-t-butoxycarbonylpiperazin-1-yl)-1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetamide in 8 mL of anhydrous dichloromethane was added 1.7 mL of trifluoroacetic acid (TFA). The reaction was stirred at room temperature for 1.75 hr then evaporated to dryness, diluted with more dichloromethane (20 mL) and re-evaporated. Residual TFA was removed with a sodium carbonate wash to give the title compound. 1H NMR (CDCl3) δ 7.58 (2H, d), 7.41 (2H, d), 6.93 (1H, d), 6.73 (1H, d), 6.60 (1H, dd), 3.75 (3H, s), 3.64 (2H, s), 3.57 (2H, m), 3.42 (2H, m), 2.75 (2H, m), 2.67 (2H, m), 2.32 (3H, s). Mass Spectrum m/e 426/428 (M+1).

Workup

  1. customthen evaporated to dryness
  2. additiondiluted with more dichloromethane (20 mL)
  3. customre-evaporated
  4. customResidual TFA was removed with a sodium carbonate
  5. washwash

Sources & evidence

ORD record
ord-83dbcf01db6845e896c05b3a2b592a68
Source dataset
uspto-grants-2008_08
Patent number
US07414067B2

Reaction notes

Loading…