N,N-Dimethylglycinamide--hydrogen chloride (1/1) → HCID 90375186, compound

HRID 1507141Notes

Reaction equation

HRID 1507141 reaction equation
Cl.[CH3:2][N:3]([CH3:8])[C:4](=[O:7])[CH2:5][NH2:6].[Si:9]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([CH:24]=O)[CH:19]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>C(N(CC)CC)C>[Si:9]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][NH:6][CH2:5][C:4]([N:3]([CH3:8])[CH3:2])=[O:7])[CH:19]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 20129283N,N-Dimethylglycinamide--hydrogen chloride (1/1)HCID 90375103HCID 90375103, compound

Product 1

HCID 90375186HCID 90375186, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

By General Procedure A from N,N-dimethylglycineamide hydrochloride, triethylamine, and 4-{[(tert-butyldimethylsilyl)oxy]methyl}pyridine-2-carbaldehyde. Purification by column chromatography (0-10% MeOH in DCM) gave the title product as yellow oil. 1H NMR (300 MHz, chloroform-d): δ ppm 8.49 (d, 1H), 7.32 (s, 1H), 7.17 (d, 1H), 4.74 (s, 2H), 3.97 (s, 2H), 3.47 (s, 2H), 2.95 (d, 6H), 0.95 (s, 9H), 0.11 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-be5c5211c1054de1974f7fbfa6db47ca
Source dataset
uspto-grants-2015_12
Patent number
US09221801B2

Reaction notes

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