Diisopropylethylamine → HCID 86717900, compound

HRID 2275823Notes

Reaction equation

HRID 2275823 reaction equation
Cl.[F:2][C:3]1([F:8])[CH2:7][CH2:6][NH:5][CH2:4]1.Br[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)C(C)C)(C)C>C(#N)C>[F:2][C:3]1([F:8])[CH2:7][CH2:6][N:5]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 249034823,3-Difluoropyrrolidine hydrochloride2×

Product 1

HCID 86717900HCID 86717900, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

900 mg of 3,3-difluoropyrrolidine hydrochloride (6.27 mmol, 1 equivalent) were initially charged in 62 ml of acetonitrile, 1475 mg of tert-butyl (2-bromoethyl)carbamate (6.58 mmol, 1.05 equivalent) and then 3.28 ml of N,N-diisopropylethylamine (2.43 g, 18.81 mmol, 3 equivalents) were added and the mixture was stirred at 80° C. overnight. 0.5 equivalent of 3,3-difluoropyrrolidine hydrochloride (450 mg, 3.14 mmol) was then added, and stirring of the reaction solution was continued at 80° C. overnight. The reaction solution was concentrated and purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate gradient: from 5/1 to pure ethyl acetate). This gave 431 mg (28% of theory) of the title compound.

Workup

  1. stirringstirring of the reaction solution
  2. waitwas continued at 80° C. overnight
  3. concentrationThe reaction solution was concentrated
  4. custompurified on a silica gel column (mobile phase: cyclohexane/ethyl acetate gradient: from 5/1 to pure ethyl acetate)

Sources & evidence

ORD record
ord-c9e7fd7b39654aaa861630cf0bbd100a
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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