Methanol → HCID 118306303, compound

HRID 521738Notes

Reaction equation

HRID 521738 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:16][CH:15]3[C:10]([C:18]4[CH:23]=[N:22][CH:21]=[CH:20][N:19]=4)([N:11]=[C:12]([NH2:17])[S:13][CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1.CO>C(=O)=O>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:16][C@@H:15]3[C@@:10]([C:18]4[CH:23]=[N:22][CH:21]=[CH:20][N:19]=4)([N:11]=[C:12]([NH2:17])[S:13][CH2:14]3)[CH2:9]2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 90121190HCID 90121190, compound

Product 1

HCID 118306303HCID 118306303, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Racemic 6-(5-fluoropyrimidin-2-yl)-7a-pyrazin-2-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine (520 mg, 1.57 mmol) is separated into its constituent enantiomers by chiral SFC (Column: Chiralcel OD-H (5μ), 21.2×250 mm; eluent: 45% methanol (0.2% diethylmethylamine) in CO2; flow: 70 mL/min at UV 260 nm). The first eluting isomer is the title compound (230 mg). ES/MS (m/e): 332 (M+1).

Sources & evidence

ORD record
ord-e9438e14eb984b6fa7285eaaa1d0a214
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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