N-Methylethylamine → HCID 136331245, compound

HRID 1958826Notes

Reaction equation

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

Participants

Reactant 2

HCID 12219N-Methylethylamine

HCID 136331244HCID 136331244, compound

Product 1

HCID 136331245HCID 136331245, compoundYield 88.6%

Procedure

The title compound (2.14 g) was prepared starting from 3-[3-(3-ethyl-4-hydroxy-5-methyl-phenyl)-[1,2,4]oxadiazol-5-yl]-5-methyl-benzaldehyde (2.13 g, 6.61 mmol) and N-ethyl-methylamine (1.56 g, 26.4 mmol) according to Method B. LC-MS: tR=0.61 min; [M+1]+=366.22; 1H NMR δ 1.06 (t, J=7.0 Hz, 3H), 1.19 (t, J=7.3 Hz, 3H), 2.14 (s, 3H), 2.28 (s, 3H), 2.41-2.48 (m, 5H), 2.65-2.72 (m, 2H), 3.54 (s, 2H), 7.46 (s, 1H), 7.67-7.71 (m, 2H), 7.89 (s, 1H), 7.93 (s, 1H), 8.93 (s, 1H).

Sources & evidence

ORD record: ord-32662f2e01894e699af63cddbd04f41d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410151B2

Reaction notes

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