Isopropanol → HCID 90265830, compound

HRID 1619069Notes

Reaction equation

HRID 1619069 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][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)=[CH:4][CH:3]=1.C(O)(C)C.[Cl:29]CCl>C(=O)=O>[ClH:29].[F:1][C:2]1[CH:7]=[CH:6][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)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6344DichloromethaneHCID 89823308HCID 89823308, compound

Product 1

HCID 90265830HCID 90265830, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Racemic 7a-(4-fluorophenyl)-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine (437 mg, 1.26 mmol) is chirally purified by SFC (Column: Chiralpak AD-H (5 u), 2.1×15 cm; eluent: 40% isopropyl alcohol (0.2% isopropylamine) in CO2; flow 70 mL/min at UV 225 nm). The second eluting isomer is dissolved in 15 mL dichloromethane and hydrogen chloride gas is bubbled through the solution for approximately 15 seconds and concentrated to give the title compound as a white solid (194 mg, 40%, >99% ee). ES/MS (m/e) 348 (M+H).

Workup

  1. customhydrogen chloride gas is bubbled through the solution for approximately 15 seconds
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-dc0ed9ec276a4850b61c919daf317437
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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