Trifluoroacetic acid → HCID 24963805, compound

HRID 499003Notes

Reaction equation

HRID 499003 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([C:16]#[C:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:13]=[CH:12][C:11]=1[O:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:34][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[Cl:33])[O:26][C:11]1[CH:12]=[CH:13][C:14]([C:16]#[C:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:15][C:10]=1[CH2:9][NH:7][CH3:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68428689HCID 68428689, compound

Product 1

HCID 24963805HCID 24963805, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(3,4-dichloro-phenoxy)-5-(4-morpholin-4-yl-but-1-ynyl)-benzyl]-methyl-carbamic acid tert-butyl ester (95.6 mg, 0.18 mmol) in DCM (2 mL) was added TFA (1 mL). After 30 min, the mixture was concentrated and the residue was purified by FCC to give the desired product (67.7 mg, 89%). MS (ESI): mass calcd. for C22H24Cl2N2O2, 418.12; m/z found, 419.3 [M+H]+. 1H NMR (CDCl3): 7.49-7.47 (m, 1H), 7.37 (d, J=8.8, 1H), 7.27 (dd, J=8.3, 2.0, 1H), 7.02 (d, J=2.8, 1H), 6.82-6.78 (m, 2H), 3.75-3.69 (m, 6H), 2.70-2.64 (m, 2H), 2.62-2.57 (m, 2H), 2.55-2.51 (m, 4H), 2.42 (s, 3H), 1.80-1.69 (m, 1H).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by FCC

Sources & evidence

ORD record
ord-b9389a98d31641079e12d34281b741f7
Source dataset
uspto-grants-2010_08
Patent number
US07767666B2

Reaction notes

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