4-Aminopyridine → HCID 59089436, compound

HRID 585748Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:18]2[C:13](=[C:14]([CH3:22])[C:15]([C:19]([OH:21])=O)=[CH:16][CH:17]=2)[S:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.[I-].ClC1C=CC=C[N+]=1C>>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:18]2[C:13](=[C:14]([CH3:22])[C:15]([C:19]([NH:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[O:21])=[CH:16][CH:17]=2)[S:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 17274-Aminopyridine

HCID 1670692-Chloro-1-methylpyridinium iodide

HCID 59089460HCID 59089460, compound

Product 1

HCID 59089436HCID 59089436, compoundYield 75.3%

Procedure

By a similar reaction operation as in Starting Material Synthetic Example 53 using (S)-4-(tert-butoxycarbonylamino)-8-methylthiochromane-7-carboxylic acid (2.00 g), 4-aminopyridine (582 mg) and 2-chloro-1-methylpyridinium iodide (2.37 g), the objective (S)-4-(tert-butoxycarbonylamino)-8-methyl-N-(4-pyridyl)thiochromane-7-carboxamide (1.86 g) was obtained as colorless crystals.

Sources & evidence

ORD record: ord-2840e12ceb904fc19e6541451653f6c4
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933305B2

Reaction notes

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