Trifluoroacetic acid → HCID 59750653, compound

HRID 422214Notes

Reaction equation

HRID 422214 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][CH2:15][CH:16]1[C:24]2[C:19](=[CH:20][C:21]([O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:34])[NH2:33])=[CH:28][N:27]=3)=[CH:22][CH:23]=2)[CH2:18][CH2:17]1)(C)(C)C>C(Cl)Cl>[NH2:14][CH2:15][CH:16]1[C:24]2[C:19](=[CH:20][C:21]([O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([NH2:33])=[O:34])=[CH:28][N:27]=3)=[CH:22][CH:23]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66673215HCID 66673215, compound

Product 1

HCID 59750653HCID 59750653, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add TFA (6.54 g, 57.4 mmol) to a suspension of [5-(5-carbamoyl-pyridin-2-yloxy)-indan-1-ylmethyl]-carbamic acid tert-butyl ester (1.05 g, 2.87 mmol) in DCM (20 ml) and stir at ambient temperature for four hours. Concentrate mixture on rotary evaporator and purify on cation exchange column (10 g, Varian) to give the title compound (519 mg) as a white solid. Mass spectrum (ion spray): m/z=284 (M+1); 1HNMR (DMSO-d6): 8.58 (s, 1H), 8.21 (d, 1H), 8.06 (br s, 1H), 7.44 (br s, 1H), 7.27 (d, 1H), 7.01 (d, 1H), 6.96 (s, 1H), 6.87 (d, 1H), 3.05 (m, 1H), 2.84 (m, 2H), 2.77 (m, 1H), 2.62 (m, 1H), 2.18 (m, 1H), 1.82 (m, 1H), 1.71 (br s, 2H).

Workup

  1. concentrationConcentrate mixture
  2. customon rotary evaporator
  3. custompurify on cation exchange column (10 g, Varian)

Sources & evidence

ORD record
ord-1a45fa47a0734fcda5e5cd330f97393e
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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