Trifluoroacetic acid → HCID 22265992, compound

HRID 489625Notes

Reaction equation

HRID 489625 reaction equation
C(OC([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([C:31]3[CH:32]=[N:33][C:34]4[C:39]([CH:40]=3)=[CH:38][C:37]([Cl:41])=[CH:36][CH:35]=4)=[O:30])[CH2:25][CH2:24]2)[CH:18]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:41][C:37]1[CH:38]=[C:39]2[C:34](=[CH:35][CH:36]=1)[N:33]=[CH:32][C:31]([C:29]([N:26]1[CH2:27][CH2:28][CH:23]([C:19]3[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=3)[CH2:16][NH2:8])[CH2:24][CH2:25]1)=[O:30])=[CH:40]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22265967HCID 22265967, compound

Product 1

HCID 22265992HCID 22265992, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-bis-(tert-butoxycarbonyl)-3-[1-(6-Chloroquinoline-3-carbonyl)-piperidin-4-yl]benzylamine (0.055 g, 0.095 mmol) was treated with a solution of 15% trifluoroacetic acid in methylene chloride (5 ml) at 0° C. The reaction was warmed to ambient temperature over 2.5 hr and the solvents were removed in vacuo. The residue was triturated with ether to yield the title compound (0.033 g, 0.087 mmol) as an amorphous solid. 1H NMR[(CD3)2SO, 500 MHz]: δ 8.95 (s, 1H), 8.44 (s, 1H), 8.20 (s, 1H), 8.07 (d, 1H), 7.84 (d, 2H), 7.23-7.40 (m, 4H), 4.67 (m, 1H), 7.34 (m, 3H), 4.75 (br m, 1H), 4.05 (m, 2H), 3.75 (br m, 1H), 3.30 (br m, 1H), 2.80-3.00 (br m, 2H), 1.90 (br m, 1H), 1.6-1.8 (br m, 3H). MS(EI): 380(M++H).

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-13ecc8342a9a42708cc4a3e28a9d62ae
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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