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 90253573, compound

HRID 1478752Notes

Reaction equation

HRID 1478752 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([NH:21][C:22]([NH:24][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[S:23])[C@H:14]([CH2:15]O)[CH2:13][C@H:12]([C:17]2([CH3:20])[CH2:19][CH2:18]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:17]3([CH3:20])[CH2:18][CH2:19]3)[CH2:13][C@H:14]1[CH2:15][S:23][C:22]([NH:24][C:25](=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[N:21]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 90253577HCID 90253577, compound

Product 1

HCID 90253573HCID 90253573, compound

Procedure

rel-N-{[(3S,4R,6R)-3-(2,4-Difluorophenyl)-4-(hydroxymethyl)-6-(1-methylcyclopropyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide (C59) was converted to the product using the method described for 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. The product was obtained as a white solid. Yield: 1.1 g, 16.8 mmol. LCMS m/z 443 [M+H+].

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-4550a675ac1043d998a02d8d27dab758
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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