Trifluoroacetic acid → HCID 79244952, compound

HRID 55888Notes

Reaction equation

HRID 55888 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:15]1([CH2:14][C:10]2[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][N:11]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90356936(2-Morpholin-4-ylmethyl-pyridin-4-yl)-carbamic acid tert-butyl ester

Product 1

HCID 79244952HCID 79244952, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 45 (150 mg, 0.513 mmol) in DCM (5 mL) was added TFA (1 mL) at 0° C. and allowed to stir at rt for 2 h. The reaction mixture was concentrated, the residue was dissolved in MeOH and treated with Ambersep-900-OH resin to basify the solution, then filtered to separate the resin and concentrated the filtrate to obtain the desired amine (90 mg, 88%) as a gummy liquid. (m/z): 194 [MH]+; 1H NMR (400 MHz, DMSO-d6) δ 7.87 (1H, d, J=5.6 Hz), 6.57 (1H, d, J=2.4 Hz), 6.33 (1H, dd, J=5.2, 2.4 Hz), 5.90 (2H, br s), 3.58-3.56 (4H, m), 3.34 (2H, s), 2.38-2.36 (4H, m).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in MeOH
  3. additiontreated with Ambersep-900-OH resin
  4. filtrationfiltered
  5. customto separate the resin
  6. concentrationconcentrated the filtrate

Sources & evidence

ORD record
ord-72a22b7dd15e4fa5b31565268cee9ff8
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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