HCID 66847793, compound → HCID 50903136, compound

HRID 2060772Notes

Reaction equation

HRID 2060772 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:16][O:15][CH2:14][CH:13]2[CH2:12][S:11][C:10]([NH2:17])=[N:9]3)=[CH:4][C:3]=1[C:18]1[CH:19]=[N:20][CH:21]=[N:22][CH:23]=1.F[C:25]1C=CC(C2C=NC=NC=2)=CC=1C12COCC1CSC(N)=N2>>[CH3:25][N:20]([CH3:21])[CH2:19][CH3:18].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]23[CH2:16][O:15][CH2:14][C@H:13]2[CH2:12][S:11][C:10]([NH2:17])=[N:9]3)=[CH:4][C:3]=1[C:18]1[CH:19]=[N:20][CH:21]=[N:22][CH:23]=1

Participants

4

Reactant 2

HCID 66847793HCID 66847793, compoundHCID 66861018HCID 66861018, compound

Product 2

HCID 11723DimethylethylamineYield 0.2%HCID 50903136HCID 50903136, compoundYield 14%

Procedure

The mixture of racemic (4aSR,7aSR)-7a-(4-fluoro-3-(pyrimidin-5-yl)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine and racemic (4aSR,7aSR)-7a-(2-fluoro-5-(pyrimidin-5-yl)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (0.231 g, 0.697 mmol) are separated using a Chiralpak AD-H 3×25 cm column eluting with 3/2 EtOH:acetonitrile with 0.2% dimethylethylamine at a flow rate of 30 mL/min., 225 nM to give (4aS,7aS)-7a-(4-fluoro-3-(pyrimidin-5-yl)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (TR=3.12) (0.032 g, 14%): ES/MS m/e: 331 (M+1) and (4aS,7aS)-7a-(2-fluoro-5-(pyrimidin-5-yl)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (TR=4.479) (0.058 g, 25%). ES/MS m/e: 331 (M+1).

Workup

  1. customare separated
  2. washeluting with 3/2 EtOH

Sources & evidence

ORD record
ord-63ba291ace3d402bb45ccf3011b073a4
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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