Triethylamine → HCID 10047715, compound

HRID 2392577Notes

Reaction equation

HRID 2392577 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[F:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])[CH2:18][CH2:17]3)=[CH:14][S:13][C:12]=2[CH:30]=1.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[C:27]([N:26]([CH2:25][CH2:24][CH2:23][CH2:22][N:19]1[CH2:18][CH2:17][N:16]([C:15]2[C:11]3[CH:10]=[CH:9][C:8]([F:7])=[CH:30][C:12]=3[S:13][CH:14]=2)[CH2:21][CH2:20]1)[C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 18980225HCID 18980225, compound

Product 1

HCID 10047715HCID 10047715, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A solution of isobutyryl chloride (2.34 g, 21.9 mmol) in dry dichloromethane (8 mL) was added over 2 minutes to a solution of N-[4-[4-(6-fluorobenzo[b]thien-3-yl)-1-piperazinyl]butyl]-acetamide (2.51 g, 7.18 mmol), triethylamine (2.18 g, 21.5 mmol), 4-dimethylaminopyridine (0.877 g, 7.18 mmol), and dry dichloromethane (50 mL) at room temperature under a nitrogen atmosphere. After 2.5 hours the reaction solution was diluted with dichloromethane (100 mL), washed with water (75 mL), dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel with 5% methanol/dichloromethane as eluent to give 2.91 g of an amber solid. Recrystallization from tert-butyl methyl ether/heptane afforded 1.52 g (50%) of the title compound as tan crystals: m.p.=98 °-99° C.

Workup

  1. washwashed with water (75 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel with 5% methanol/dichloromethane as eluent

Sources & evidence

ORD record
ord-54362965a40d4ae181b5f2dab8a0e07e
Source dataset
uspto-grants-1998_09
Patent number
US05801176

Reaction notes

Loading…