4-Aminopyridine → HCID 59089453, compound

HRID 585765Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:18]2[C:13](=[CH:14][C:15]([C:21]([OH:23])=O)=[C:16]([O:19][CH3:20])[CH:17]=2)[S:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1.[I-].ClC1C=CC=C[N+]=1C>>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:18]2[C:13](=[CH:14][C:15]([C:21]([NH:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[O:23])=[C:16]([O:19][CH3:20])[CH:17]=2)[S:12][CH2:11][CH2:10]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 3

HCID 17274-Aminopyridine

HCID 1670692-Chloro-1-methylpyridinium iodide

HCID 59089475HCID 59089475, compound

Product 1

HCID 59089453HCID 59089453, compoundYield 74.6%

Procedure

By a similar reaction operation as in Starting Material Synthetic Example 53 using (S)-4-(tert-butoxycarbonylamino)-6-methoxythiochromane-7-carboxylic acid (300 mg), 4-aminopyridine (83.3 mg) and 2-chloro-1-methylpyridinium iodide (271 mg), the objective (S)-4-(tert-butoxycarbonylamino)-6-methoxy-N-(4-pyridyl)thiochromane-7-carboxamide (274 mg) was obtained as a pale-red amorphous solid.

Sources & evidence

ORD record: ord-07db32aeed6d4adb8478ae97a692f9ab
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933305B2

Reaction notes

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