Ethanol → HCID 90121178, compound

HRID 521736Notes

Reaction equation

HRID 521736 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[CH2:16][N:15]([C:17]4[N:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=4)[CH2:14][CH:13]2[CH2:12][S:11][C:10]([NH2:24])=[N:9]3)=[N:6][CH:7]=1.C(O)C>C(=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]23[CH2:16][N:15]([C:17]4[N:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=4)[CH2:14][C@H:13]2[CH2:12][S:11][C:10]([NH2:24])=[N:9]3)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 90121192HCID 90121192, compound

Product 1

HCID 90121178HCID 90121178, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Racemic 7a-(5-fluoro-2-pyridyl)-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine (60 mg, 0.172 mmol) is separated into its constituent enantiomers by chiral SFC (Column: Chiralpak AD-H (5μ), 21.2×250 mm; eluent: 40% ethanol (0.2% diethylmethylamine) in CO2; flow: 70 mL/min at UV 260 nm). The second eluting isomer is the title compound (23.8 mg). ES/MS (m/e): 349 (M+1).

Sources & evidence

ORD record
ord-b9e489f8c08f4afba2d72e5d3292f8ca
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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