Isopropanol → HCID 90121151, compound

HRID 521733Notes

Reaction equation

HRID 521733 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:19]=[N:20][CH:21]=[CH:22][CH:23]=4)([N:11]=[C:12]([NH2:17])[S:13][CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1.C(O)(C)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:19]=[N:20][CH:21]=[CH:22][CH:23]=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 3776IsopropanolHCID 90111905HCID 90111905, compound

Product 1

HCID 90121151HCID 90121151, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Racemic 6-(5-fluoropyrimidin-2-yl)-7a-(3-pyridyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine (137 mg, 0.415 mmol) is separated into its constituent enantiomers by chiral SFC (Column: Chiralpak AD-H (5μ), 21.2×250 mm; eluent: 35% isopropanol (0.2% diethylmethylamine) in CO2; flow: 70 mL/min at UV 260 nm). The second eluting isomer is the title compound (19 mg). ES/MS (m/e): 331 (M+1).

Sources & evidence

ORD record
ord-a99e989c3be3447dbf281bc3cea6cef0
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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