Triethylamine → 8-((1,4-Oxazepan-4-yl)methyl)-6-(4-methoxybenzyl)thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 707460Notes

Reaction equation

HRID 707460 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[C:13]3[S:14][C:15]([CH:17]=O)=[CH:16][C:12]=3[C:11]3=[N:19][CH:20]=[N:21][N:10]3[C:9]2=[O:22])=[CH:5][CH:4]=1.Cl.[O:26]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(N(CC)CC)C.[Na]>ClCCl>[O:26]1[CH2:32][CH2:31][CH2:30][N:29]([CH2:17][C:15]2[S:14][C:13]3[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:24][CH:23]=4)[C:9](=[O:22])[N:10]4[N:21]=[CH:20][N:19]=[C:11]4[C:12]=3[CH:16]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5360545SodiumHCID 230902141,4-Oxazepane hydrochlorideHCID 867053726-(4-Methoxybenzyl)-5-oxo-5,6-dihydrothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-8-carbaldehyde

Product 1

HCID 1184855438-((1,4-Oxazepan-4-yl)methyl)-6-(4-methoxybenzyl)thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-oneYield 51.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-((1,4-oxazepan-4-yOmethyl)-6-(4-methoxybenzyl)thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (29). To a mixture of 6-(4-methoxybenzyl)-5-oxo-5,6-dihydrothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-8-carbaldehyde (50 mg, 0.15 mmol) and 1,4-oxazepane hydrochloride (30 mg, 0.22 mmol) in dichloromethane (2 ml) was added triethylamine (25 μl, 0.18 mmol). After 5 minutes of stifling, sodium triacetoxyhydroborate (47 mg, 0.22 mmol) was added. The resulting mixture was stirred at room temperature. After 4 hours, the mixture was concentrated under reduced pressure. The resulting residue was taken up in DMSO (2 mL), filtered and purified directly by reverse phase chromatography to yield the above product (33 mg, 41%) as a white solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. filtrationfiltered
  3. custompurified directly by reverse phase chromatography

Sources & evidence

ORD record
ord-fed250c57bd24ab78ea830fcdd9ac9b1
Source dataset
uspto-grants-2015_11
Patent number
US09175010B2

Reaction notes

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