HCID 89832349, compound → HCID 89832354, compound

HRID 1619059Notes

Reaction equation

HRID 1619059 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[CH2:16][N:15]([C:17]3[N:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=3)[CH2:14][CH:13]1[CH2:12][S:11][C:10]([NH2:24])=[N:9]2>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]12[CH2:16][N:15]([C:17]3[N:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=3)[CH2:14][C@H:13]1[CH2:12][S:11][C:10]([NH2:24])=[N:9]2

Participants

3

Reactant 1

HCID 89832349HCID 89832349, compound

Product 1

HCID 89832354HCID 89832354, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic 7a-(2-fluorophenyl)-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine (361 mg, 1.04 mmol) is purified by chiral HPLC (Column: Chiralpak AD-H (5 u), 3×25 cm; eluent: 100% methanol (0.2% isopropylamine); flow 30 mL/min at UV 225 nm. The second eluting isomer is the title compound (114 mg, 32%, 99% ee). Rt=4.887 minutes; column: Chiralpak AD-H 0.46×15 cm; eluent: 100% methanol (0.2% isopropylamine) in CO2; flow: 1 mL/min at UV 225 nm.

Sources & evidence

ORD record
ord-b4f390aa4fc14f899cc5943ddeed6459
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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