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

HRID 422211Notes

Reaction equation

HRID 422211 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-87bf88c9e6e148f2b6be3f722b3c4fb5
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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