Hydrochloric Acid → HCID 57504946, compound

HRID 2060806Notes

Reaction equation

HRID 2060806 reaction equation
[ClH:1].CCOCC.[NH2:7][C:8]1[S:9][CH2:10][C@@H:11]2[CH2:16][C@@H:15]([OH:17])[CH2:14][C@:12]2([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=3)[CH:21]=[CH:22][CH:23]=2)[N:13]=1>ClCCl.CO>[ClH:1].[NH2:7][C:8]1[S:9][CH2:10][C@@H:11]2[CH2:16][C@@H:15]([OH:17])[CH2:14][C@:12]2([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=3)[CH:21]=[CH:22][CH:23]=2)[N:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 57504947HCID 57504947, compound

Product 1

HCID 57504946HCID 57504946, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-((4aR,6R,7aS)-6-hydroxy-7a-(3′-methoxybiphenyl-3-yl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl)benzamide (0.061 g, 0.133 mmol), o-methylhydroxylamine hydrochloride (0.111 g, 1.3 mmol) and pyridine (0.105 g, 1.30 mmol) in ethanol (5 mL) is heated to 50° C. for 15 h. The mixture is concentrated under reduced pressure. The crude product is purified by silica gel chromatography eluting with 0.5% to 10% NH3 (7 N solution in methanol) in dichloromethane over 30 minutes to afford the title compound as a freebase (0.041 g, 87%). ES/MS m/e: 355 (M+1). A 1 N solution of HCl in Et2O (0.139 mL, 0.139 mmol) is added to a solution of (4aR,6R,7aS)-2-amino-7a-(3′-methoxybiphenyl-3-yl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-6-ol (0.041 g, 0.116 mmol) in minimal dichloromethane and methanol. The solvent is removed under reduced pressure to give the title compound (0.045 g, 86%). ES/MS m/e: 355 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-120a688f14a341279ffda7b625b5759c
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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