Trifluoroacetic acid → HCID 86605018, compound

HRID 706354Notes

Reaction equation

HRID 706354 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([C:29]([C:31]3[CH:36]=[CH:35][N:34]=[C:33]([Cl:37])[CH:32]=3)=[O:30])[CH2:21]2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:37][C:33]1[CH:32]=[C:31]([C:29]([N:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18]3([CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)[CH2:21]2)=[O:30])[CH:36]=[CH:35][N:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58046556HCID 58046556, compound

Product 1

HCID 86605018HCID 86605018, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (30 ml) was added to a solution of solution of 1-(2-chloropyridin-4-yl)carbonylspiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butyl ester (2.3 g) in anhydrous dichloromethane (50 ml), the solution darkening upon addition. The reaction was left as such for 15 min. The reaction mixture was evaporated in vacuo and the dark residue re-suspended in dry ether (100 ml). The residue was triturated until it became a free-flowing beige precipitate. The precipitate was collected by filtration and dried in a stream of nitrogen to give 2.28 g (96%) of the desired amine salt. M.p. 245° C. (decomposition). 1H NMR (400 MHz, d6-DMSO) 1.8 (m, 2H), 1.9 (m, 2H), 2.9 (m, 2H), 3.25 (m, 2H), 3.98 (s, 2H), 7.15-7.3 (m, 2H), 7.24 (d, J=8 Hz, 1H), 7.56 (d, J=7 Hz, 1H), 7.62 (s, 1H), 8.1 (br s, 1H), 8.56 (d, J=7 Hz, 1H), 8.8 (br s, 2H). MS (ES+) 328/330 (M+H+).

Workup

  1. additionthe solution darkening upon addition
  2. customThe reaction mixture was evaporated in vacuo
  3. customThe residue was triturated until it
  4. filtrationThe precipitate was collected by filtration
  5. customdried in a stream of nitrogen

Sources & evidence

ORD record
ord-bd2d9cb2c12b44fa81eed288040e9763
Source dataset
uspto-grants-2015_11
Patent number
US09174987B2

Reaction notes

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