Trifluoroacetic acid → HCID 69320728, compound

HRID 747964Notes

Reaction equation

HRID 747964 reaction equation
[C:1](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][CH: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)[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66673215HCID 66673215, compound

Product 1

HCID 69320728HCID 69320728, compoundYield 60.8%

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), 8.00 (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-9de8c024033a4fdcbc23bf82aacd7180
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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