Methanol → HCID 90121188, compound

HRID 521734Notes

Reaction equation

HRID 521734 reaction equation
[F:1][C:2]1[C:3]([CH:24]([CH3:26])[CH3:25])=[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.CO>C(=O)=O>[F:1][C:2]1[C:3]([CH:24]([CH3:26])[CH3:25])=[N:4][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:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 90121177HCID 90121177, compound

Product 1

HCID 90121188HCID 90121188, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Racemic 6-(5-fluoro-4-isopropyl-pyrimidin-2-yl)-7a-(3-pyridyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine (210 mg, 0.564 mmol) is separated into its constituent enantiomers by chiral SFC (Column: Chiralcel OD-H (5μ), 21.2×250 mm; eluent: 25% methanol (0.2% diethylmethylamine) in CO2; flow: 70 mL/min at UV 260 nm). The first eluting isomer is further purified again by chiral SFC (Column: Chiralcel OD-H (5μ), 21.2×250 mm; eluent: 15% methanol (0.2% diethylmethylamine) in CO2; flow: 70 mL/min at UV 260 nm) to obtain the title compound (71 mg). ES/MS (m/e): 373 (M+1).

Workup

  1. customThe first eluting isomer is further purified again by chiral SFC (Column: Chiralcel OD-H (5μ), 21.2×250 mm; eluent: 15% methanol (0.2% diethylmethylamine) in CO2; flow: 70 mL/min at UV 260 nm)

Sources & evidence

ORD record
ord-133d7b92d20e4c6d8a14ddd59db07d45
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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