Diisopropylethylamine → HCID 86727065, compound

HRID 1502017Notes

Reaction equation

HRID 1502017 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([F:14])=[CH:7][C:8]([F:13])=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:4].[OH:15][CH2:16][C@H:17]1[NH:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1.CCN(C(C)C)C(C)C>C1COCC1>[C:10]([C:9]1[C:8]([F:13])=[CH:7][C:6]([F:14])=[C:5]([C:3](=[O:4])[CH2:2][N:22]2[CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:18][C@H:17]2[CH2:16][OH:15])[CH:12]=1)#[N:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 86727066HCID 86727066, compound

Product 1

HCID 86727065HCID 86727065, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 5-(bromoacetyl)-2,4-difluorobenzonitrile (2.5 g, 9.6 mmol), tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate (2.1 g, 9.6 mmol) and DIEA (1.90 g, 14.4 mmol) in 50 mL of THF was stirred at 20° C. for 10 hours. The reaction mixture was poured into ice water and extracted with EtOAc (3×200 mL). The combined organic layers were washed with water and brine, dried and concentrated. The residue was purified by column chromatography eluting with 5% MeOH in DCM to afford the title compound.

Workup

  1. extractionextracted with EtOAc (3×200 mL)
  2. washThe combined organic layers were washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-e110a84554b44ab0a3ce0f57ad0d76aa
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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