Triethyl orthoacetate → HCID 90022611, compound

HRID 56226Notes

Reaction equation

[NH2:1]/[C:2](/[CH3:29])=[CH:3]\[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH3:27])([CH3:26])[CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)=[C:9]([Cl:28])[CH:8]=1)=[O:5].[C:30](OCC)(OCC)(OCC)[CH3:31]>>[Cl:28][C:9]1[CH:8]=[C:7]([N:6]2[C:4](=[O:5])[CH:3]=[C:2]([CH3:29])[N:1]=[C:30]2[CH3:31])[CH:12]=[CH:11][C:10]=1[NH:13][C:14]([CH3:26])([CH3:27])[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1

Participants

Reactant 2

HCID 66221Triethyl orthoacetate

HCID 117966096HCID 117966096, compound

Product 1

HCID 90022611HCID 90022611, compoundYield 76%

Conditions

Temperature: 150 °C

Procedure

A mixture of (Z)-3-amino-N-(3-chloro-4-((2-methyl-1-(naphthalen-2-yl)propan-2-yl)amino)phenyl)but-2-enamide and (2.0 g, 4.90 mmol) and triethyl orthoacetate (20 mL) was stirred at 150° C. for 12 h. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (1.59 g, 76%). The compound was characterized by the following spectroscopic data:

Workup

temperatureThe mixture was cooled to rt
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record: ord-8ef6bd6c3a0946bfbc1993ef0b2d6b5b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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