N-({(3S,4R,6R)-6-cyclopropyl-3-(2,4-difluorophenyl)-4-[(1S)-1-hydroxyethyl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamide → rel-N-({(3S,4R,6R)-6-cyclopropyl-3-(2,4-difluorophenyl)-4-[(1R)-2-fluoro-1-hydroxyethyl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamide

HRID 1478741Notes

Reaction equation

HRID 1478741 reaction equation
[NH2:1][C@@:2]1([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:7][O:6][C@@H:5]([CH:8]2[CH2:10][CH2:9]2)[CH2:4][C@H:3]1[C@@H:11]([OH:14])[CH2:12][F:13].C1([C@@H]2OC[C@@](N[C:41]([NH:43][C:44](=[O:51])[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[S:42])(C3C=CC(F)=CC=3F)[C@H]([C@@H](O)C)C2)CC1>>[CH:8]1([C@@H:5]2[O:6][CH2:7][C@@:2]([NH:1][C:41]([NH:43][C:44](=[O:51])[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[S:42])([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[C@H:3]([C@@H:11]([OH:14])[CH2:12][F:13])[CH2:4]2)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 90253450N-({(3S,4R,6R)-6-cyclopropyl-3-(2,4-difluorophenyl)-4-[(1S)-1-hydroxyethyl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamideHCID 90253568rel-(1R)-1-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]-2-fluoroethanol

Product 1

HCID 90253571rel-N-({(3S,4R,6R)-6-cyclopropyl-3-(2,4-difluorophenyl)-4-[(1R)-2-fluoro-1-hydroxyethyl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamide

Procedure

Conversion of rel-(1R)-1-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]-2-fluoroethanol (C45) to the product was carried out according to the method described for synthesis of N-({(3S,4R,6R)-6-cyclopropyl-3-(2,4-difluorophenyl)-4-[(1S)-1-hydroxyethyl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamide (C30) in Example 3. The product was obtained as a solid. Yield: 155 mg, 0.324 mmol, 60%. LCMS m/z 479.2 [M+H+].

Workup

  1. customThe product was obtained as a solid

Sources & evidence

ORD record
ord-c1bb2156ca53496c9c78ef339404a51e
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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