3-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]benzonitrile → N-{[(3S,4R,6S)-3-(3-cyanophenyl)-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide

HRID 1496747Notes

Reaction equation

HRID 1496747 reaction equation
N[C@]1(C2C=C(C=CC=2)C#N)[C@H](CO)C[C@H](C)OC1.Cl[C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=1[C@@:28]1([NH:37][C:38]([NH:40][C:41](=[O:48])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[S:39])[C@H:33]([CH2:34][OH:35])[CH2:32][C@H:31]([CH3:36])[O:30][CH2:29]1>>[C:26]([C:23]1[CH:22]=[C:21]([C@@:28]2([NH:37][C:38]([NH:40][C:41](=[O:48])[C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[S:39])[C@H:33]([CH2:34][OH:35])[CH2:32][C@H:31]([CH3:36])[O:30][CH2:29]2)[CH:20]=[CH:25][CH:24]=1)#[N:27]

Participants

3

Reactant 2

HCID 867212983-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]benzonitrileHCID 86721302N-{[(3S,4R,6S)-3-(2-chloro-5-cyanophenyl)-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide

Product 1

HCID 86721301N-{[(3S,4R,6S)-3-(3-cyanophenyl)-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide

Procedure

3-[(3S,4R,6S)-3-Amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]benzonitrile (C22) was converted to the product using the method described for the synthesis of N-{[(3S,4R,6S)-3-(2-chloro-5-cyanophenyl)-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide (C19) in Example 6. The resulting product was used in the next step without further purification. Yield: 118 mg, 0.288 mmol, 68%. LCMS m/z 410.2 [M+H+].

Workup

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

Sources & evidence

ORD record
ord-3fa2288c3927471aaa87195f2183f468
Source dataset
uspto-grants-2015_12
Patent number
US09198917B2

Reaction notes

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