4-Aminopyridine → (S)-4-(tert-butoxycarbonylamino)-6-methyl-N-(4-pyridyl)thiochromane-7-carboxamide

HRID 585752Notes

Reaction equation

HRID 585752 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:18]2[C:13](=[CH:14][C:15]([C:20]([OH:22])=O)=[C:16]([CH3:19])[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](=[CH:14][C:15]([C:20]([NH:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[O:22])=[C:16]([CH3:19])[CH:17]=2)[S:12][CH2:11][CH2:10]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 3

HCID 17274-AminopyridineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 59089485(S)-4-(tert-butoxycarbonylamino)-6-methylthiochromane-7-carboxylic acid

Product 1

HCID 59089457(S)-4-(tert-butoxycarbonylamino)-6-methyl-N-(4-pyridyl)thiochromane-7-carboxamideYield 87.4%

Procedure

By a similar reaction operation as in Starting Material Synthetic Example 53 using (S)-4-(tert-butoxycarbonylamino)-6-methylthiochromane-7-carboxylic acid (1.00 g), 4-aminopyridine (321 mg) and 2-chloro-1-methylpyridinium iodide (949 mg), the objective (S)-4-(tert-butoxycarbonylamino)-6-methyl-N-(4-pyridyl)thiochromane-7-carboxamide (1.08 g) was obtained as a pale-brown amorphous solid.

Sources & evidence

ORD record
ord-a63e5f2ae2654d0f88f5561371f85e9d
Source dataset
uspto-grants-2005_08
Patent number
US06933305B2

Reaction notes

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