Ethanol → HCID 90121207, compound

HRID 521737Notes

Reaction equation

HRID 521737 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]=[CH:22][N:21]=[CH:20][CH:19]=4)([N:11]=[C:12]([NH2:17])[S:13][CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1.C(O)C>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]=[CH:22][N:21]=[CH:20][CH: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 702EthanolHCID 90121195HCID 90121195, compound

Product 1

HCID 90121207HCID 90121207, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Racemic 6-(5-fluoropyrimidin-2-yl)-7a-(4-pyridyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine (185 mg, 0.56 mmol) is separated into its constituent enantiomers by chiral SFC (Column: Chiralcel OJ-H (5μ), 21.2×250 mm; eluent: 25% ethanol (0.2% diethylmethylamine) in CO2; flow: 70 mL/min at UV 260 nm). The second eluting isomer is the title compound (40 mg). ES/MS (m/e): 331 (M+1).

Sources & evidence

ORD record
ord-acb7160d54cb4c74a3f11e592a054310
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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