N-[(4aR,6R,8aS)-6-[(benzyloxy)methyl]-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide → HCID 90253541, compound

HRID 1478778Notes

Reaction equation

HRID 1478778 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([NH:22][C:23]([NH:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[S:24])[C@H:14]([CH2:15]O)[CH2:13][C@H:12]([C@@H:17]2[CH2:21][CH2:20][CH2:19][O:18]2)[O:11][CH2:10]1.C(OC[C@@H]1OC[C@]2(C3C=CC(F)=CC=3F)N=C(NC(=O)C3C=CC=CC=3)SC[C@@H]2C1)C1C=CC=CC=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:10][O:11][C@@H:12]([C@@H:17]3[CH2:21][CH2:20][CH2:19][O:18]3)[CH2:13][C@H:14]1[CH2:15][S:24][C:23]([NH:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[N:22]2

Participants

3

Reactant 2

HCID 86729526N-[(4aR,6R,8aS)-6-[(benzyloxy)methyl]-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamideHCID 90253548HCID 90253548, compound

Product 1

HCID 90253541HCID 90253541, compound

Procedure

N-({(3S,4R,6R)-3-(2,4-Difluorophenyl)-4-(hydroxymethyl)-6-[(2S)-tetrahydrofuran-2-yl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamide (C102) was converted to the product using the method described for the synthesis of N-[(4aR,6R,8aS)-6-[(benzyloxy)methyl]-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (C8) in Preparation P1. Yield: 1.0 g, 2.2 mmol, 87%. LCMS m/z 458.9 [M+H+].

Sources & evidence

ORD record
ord-5674aaa42edd454285e149c7b72cbc9c
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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