Trifluoroacetic acid → HCID 68743041, compound

HRID 2093626Notes

Reaction equation

HRID 2093626 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH:22][C:23](=[O:42])[C:24]2[CH:29]=[CH:28][C:27]([C:30]3[O:31][C:32]4[C:38]([CH3:39])=[CH:37][C:36]([C:40]#[N:41])=[CH:35][C:33]=4[N:34]=3)=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[C:40]([C:36]1[CH:37]=[C:38]([CH3:39])[C:32]2[O:31][C:30]([C:27]3[CH:26]=[CH:25][C:24]([C:23]([NH:22][CH2:21][CH:18]4[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]4)=[O:42])=[CH:29][CH:28]=3)=[N:34][C:33]=2[CH:35]=1)#[N:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68786775HCID 68786775, compound

Product 1

HCID 68743041HCID 68743041, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trifluoroacetic acid (2 ml) in dichloromethane (2 ml) was added 4 tert-butyl-4-({[4-(5-cyano-7-methyl-1,3-benzoxazol-2-yl)benzoyl]amino}methyl)piperidine-1-carboxylate (68 mg). The mixture was stirred for 1 h, and then concentrated in vacuo to provide 4-(5-cyano-7-methyl-1,3-benzoxazol-2-yl)-N-(piperidin-4-ylmethyl)benzamide (67 mg. 99%). Half of this sample was added to potassium carbonate (19 mg) in ethanol. 4-Trifluoromethylbenzyl bromide (17 mg) was added and the mixture was heated to 70° C. for 4 h. The sample was cooled to room temperature, concentrated in vacuo, and was purified via preparative thin-layer chromatography (Rf=0.58 in 1:1 hexanes-ethyl acetate) to provide the title compound (31 mg, 84%). Mass spectrum (ESI) 533.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.34 (d, J=8.5 Hz, 2H), 7.94 (d, J=8.4 Hz, 2H), 7.94 (s, 1H), 7.57 (d, J=7.6 Hz, 2H), 7.48 (s, 1H), 7.44 (d, J=7.6 Hz, 2H), 6.23 (t, J=6.4 Hz, 1H), 3.55 (s, 2H), 3.42 (t, J=6.2 Hz, 2H), 2.99 (m, 2H), 2.65 (s, 6H), 2.03 (m, 2H), 1.76, m (2H), 1.42 (m, 3H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0413301d56a443ebb13b0a5f3e2d6617
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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