4-Bromobutyronitrile → HCID 88962056, compound

HRID 529347Notes

Reaction equation

HRID 529347 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].C(N(CC)C(C)C)(C)C.[F:16][C:17]([F:38])([F:37])[C:18]([N:20]([CH:28]1[CH2:30][CH:29]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:19]>C(#N)C>[C:5]([CH2:4][CH2:3][CH2:2][N:25]1[CH2:24][CH2:23][CH:22]([CH2:21][N:20]([CH:28]2[CH2:30][CH:29]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:18](=[O:19])[C:17]([F:16])([F:37])[F:38])[CH2:27][CH2:26]1)#[N:6]

Participants

5

Reactant 3

HCID 214124-BromobutyronitrileHCID 81531DiisopropylethylamineHCID 88962016HCID 88962016, compound

Product 1

HCID 88962056HCID 88962056, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Added 4-bromobutanenitrile (100 mg, 0.674 mmol) to a solution of N,N-diisopropylethylamine (0.353 mL, 2.022 mmol), 2,2,2-trifluoro-N-(2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide (220 mg, 0.674 mmol) in acetonitrile (25 mL) and heated to reflux for 16 hours. Concentrated on rotovap and the residue was purified via Biotage (0% to 100% EtOAc:Hex; then 0% to 20% MeOH:DCM to get off more product: 10 g-HP—silica gel column).

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. concentrationConcentrated on rotovap
  4. customthe residue was purified via Biotage (0% to 100% EtOAc
  5. customthen 0% to 20% MeOH:DCM to get off more product

Sources & evidence

ORD record
ord-7fef4aee0f104634b863ed114400ec49
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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