Acetic Acid → HCID 86649393, compound

HRID 2196073Notes

Reaction equation

HRID 2196073 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](C=O)=[CH:3][CH:2]=1.[C:9](O)(=O)[CH3:10].[CH2:13]([N:15]1[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[C:19](=[O:25])[N:18]([CH3:26])[C:17]2[CH:27]=[C:28]([O:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37]C3C=NC=CC=3)[CH:29]=[CH:30][C:16]1=2)[CH3:14].[Na]>ClCCl.ClCCCl>[CH2:13]([N:15]1[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[C:19](=[O:25])[N:18]([CH3:26])[C:17]2[CH:27]=[C:28]([O:31][CH2:32][CH2:33][CH2:34][N:35]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH2:36][CH2:37][CH2:4][C:3]3[CH:2]=[N:1][CH:6]=[CH:9][CH:10]=3)[CH:29]=[CH:30][C:16]1=2)[CH3:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 133894-PyridinecarboxaldehydeHCID 5360545SodiumHCID 686730021-Ethyl-3,3,5-trimethyl-7-[3-(2-pyridin-3-ylethylamino) propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 86649393HCID 86649393, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

4-Pyridinecarbaldehyde (1.18 ml, 12.5 mmol) and a catalytic amount of acetic acid were added to a 1,2-dichloroethane solution (40 ml) of 1-ethyl-3,3,5-trimethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (4.44 g, 10.5 mmol), and stirred for 30 minutes. Sodium triacetoxyhydroborate (3.33 g, 15.7 mmol) was added to the resulting mixture, and stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with water and a saturated sodium chloride aqueous solution in this order, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (ethyl acetate:methanol=1:0→9:1). The purified product was concentrated under reduced pressure to thereby obtain 4.73 g (yield: 88%) of 1-ethyl-3,3,5-trimethyl-7-{3-[(2-pyridin-3-ylethyl)pyridin-4-yl methylamino]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a pale yellow oil.

Workup

  1. stirringstirred at room temperature overnight
  2. washwashed with water
  3. dry with materiala saturated sodium chloride aqueous solution in this order, then dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (ethyl acetate:methanol=1:0→9:1)
  6. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f6d06e1b43f4978bc2db43aff4cae24
Source dataset
uspto-grants-2012_12
Patent number
US08338406B2

Reaction notes

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