N-{[(3S,4R,6S)-3-(3-cyanophenyl)-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide → N-[(4aR,6S,8aS)-8a-(3-cyanophenyl)-6-methyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 1496748Notes

Reaction equation

HRID 1496748 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C@@:9]2([NH:18][C:19]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[S:20])[C@H:14]([CH2:15]O)[CH2:13][C@H:12]([CH3:17])[O:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].ClC1C=CC(C#N)=CC=1[C@]12CO[C@@H](C)C[C@H]1CSC(NC(=O)C1C=CC=CC=1)=N2>>[C:1]([C:3]1[CH:4]=[C:5]([C@:9]23[CH2:10][O:11][C@@H:12]([CH3:17])[CH2:13][C@H:14]2[CH2:15][S:20][C:19]([NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:18]3)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 86721301N-{[(3S,4R,6S)-3-(3-cyanophenyl)-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]carbamothioyl}benzamideHCID 86762644N-[(4aR,6S,8aS)-8a-(2-chloro-5-cyanophenyl)-6-methyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Product 1

HCID 86762643N-[(4aR,6S,8aS)-8a-(3-cyanophenyl)-6-methyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Procedure

N-{[(3S,4R,6S)-3-(3-Cyanophenyl)-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide (C23) was converted to the product using the method described for the synthesis of N-[(4aR,6S,8aS)-8a-(2-chloro-5-cyanophenyl)-6-methyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (C20) in Example 6. The resulting product was used in the next step without further purification. Yield: 45.0 mg, 0.115 mmol, 40%. LCMS m/z 392.2 [M+H+].

Workup

  1. customThe resulting product was used in the next step without further purification

Sources & evidence

ORD record
ord-522243b34918435c857701d95fe30822
Source dataset
uspto-grants-2015_12
Patent number
US09198917B2

Reaction notes

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