Trifluoroacetic acid → HCID 58154512, compound

HRID 2359392Notes

Reaction equation

HRID 2359392 reaction equation
C1(C2C=CC3C(=C(N)C=CC=3)N=2)C=CC=CC=1.C(OC(N1CCC(C(O)=O)CC1)=O)(C)(C)C.[C:34]1([C:40]2[CH:49]=[CH:48][C:47]3[C:42](=[C:43]([NH:50][C:51]([CH:53]4[CH2:58][CH2:57][N:56](C(OC(C)(C)C)=O)[CH2:55][CH2:54]4)=[O:52])[CH:44]=[CH:45][CH:46]=3)[N:41]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:34]1([C:40]2[CH:49]=[CH:48][C:47]3[C:42](=[C:43]([NH:50][C:51]([CH:53]4[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]4)=[O:52])[CH:44]=[CH:45][CH:46]=3)[N:41]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 199558612-Phenylquinolin-8-amineHCID 66884536HCID 66884536, compound

Product 1

HCID 58154512HCID 58154512, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phenylquinolin-8-amine (60 mg, 0.27 mmol) was subjected to the same general amide coupling procedure outlined above using 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid. The resulting intermediate, namely tert-butyl 4-(2-phenylquinolin-8-ylcarbamoyl)piperidine-1-carboxylate, was further treated with 2 mL of 25% TFA in CH2Cl2 for 6 h. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by preparative HPLC (using aqueous CH3CN that has been buffered with 0.1% TFA) to afford 25 mg of the product. MS (ESI) calcd for C21H21N3O (m/z): 331.17. found: 332 [M+1].

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by preparative HPLC (using aqueous CH3CN that has been buffered with 0.1% TFA)

Sources & evidence

ORD record
ord-60d59b3f1d204175a0abe8bfb0a00861
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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