Triethylamine → HCID 90375141, compound

HRID 1507153Notes

Reaction equation

HRID 1507153 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH:16]=O)[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[NH2:19][CH2:20]/[CH:21]=[CH:22]/[CH2:23][N:24]([CH3:26])[CH3:25].C(N(CC)CC)C>>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][NH:19][CH2:20]/[CH:21]=[CH:22]/[CH2:23][N:24]([CH3:26])[CH3:25])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 82667976HCID 82667976, compoundHCID 90375103HCID 90375103, compound

Product 1

HCID 90375141HCID 90375141, compound

Procedure

By General Procedure A from 4-{[(tert-butyldimethylsilyl)oxy]methyl}pyridine-2-carbaldehyde (1.0 equiv.), [(2E)-4-aminobut-2-en-1-yl]dimethylamine hydrochloride (1.0 equiv.), and triethylamine (1.0 equiv.). Purification by column chromatography (0-10% MeOH in DCM) gave the title product as yellow oil. 1H NMR (300 MHz, chloroform-d): δ ppm 8.45 (d, 1H), 7.20 (s, 1H), 7.11 (d, 1H), 5.67 (m, 2H), 4.68 (s, 2H), 3.85 (s, 2H), 2.89 (s, 2H), 2.19 (s, 6H), 0.89 (m, 9H), 0.07 (m, 6H).

Workup

  1. customPurification by column chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-a07bda2456d14fc0a47468c269c48161
Source dataset
uspto-grants-2015_12
Patent number
US09221801B2

Reaction notes

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