Trifluoroacetic acid → 6-(2-Amino-indan-5-yloxy)-nicotinamide

HRID 747961Notes

Reaction equation

HRID 747961 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31](=[O:33])[NH2:32])=[CH:27][N:26]=3)[CH:21]=2)[CH2:16]1)(C)(C)C>C(Cl)Cl>[NH2:14][CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([NH2:32])=[O:33])=[CH:27][N:26]=3)[CH:21]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66672889HCID 66672889, compound

Product 1

HCID 597506556-(2-Amino-indan-5-yloxy)-nicotinamideYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add TFA (5.37 g, 47.1 mmol) to a suspension of [5-(5-carbamoyl-pyridin-2-yloxy)-indan-2-yl]-carbamic acid tert-butyl ester (870 mg, 2.35 mmol) in DCM (30 ml) and stir at ambient temperature overnight. Concentrate mixture on rotary evaporator and purify on cation exchange column (5 g, Varian) to give the title compound (479 mg) as a white solid. Mass spectrum (ion spray): m/z=270 (M+1); 1HNMR (MeOH-d4): 8.61 (s, 1H), 8.22 (d, 1H), 7.24 (d, 1H), 6.98 (s, 1H), 6.94 (d, 1H), 6.90 (d, 1H), 3.80 (m, 1H), 3.18 (m, 2H), 2.72 (m, 2H).

Workup

  1. concentrationConcentrate mixture
  2. customon rotary evaporator
  3. custompurify on cation exchange column (5 g, Varian)

Sources & evidence

ORD record
ord-ad744919e51045d0a3de1b1b7ab318e5
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

Loading…