Isopropanol → HCID 90265830, compound

HRID 338168Notes

Reaction equation

HRID 338168 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 (5u), 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-fbaeefc600684948a2aff02375a220b0
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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