2-[(1R)-1-Chloroethyl]-3-fluoropyridine → HCID 25064543, compound

HRID 2422184Notes

Reaction equation

HRID 2422184 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:19]=1.Cl[C@@H:21]([C:23]1[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=1)[CH3:22]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:12][OH:13])=[N:8][C:7]([S:18][C@H:21]([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=3)[CH3:22])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 598688232-[(1R)-1-Chloroethyl]-3-fluoropyridineHCID 178445911HCID 178445911, compound

Product 1

HCID 25064543HCID 25064543, compoundYield 47%

Procedure

The title compound was prepared using General method A starting from (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (348 mg, 1.16 mmol) and 2-((R)-1-chloroethyl)-3-fluoro-pyridine (240 mg, 1.5 mmol). Purification by flash column chromatography (eluent DCM: methanol gradient) resulted in 190 mg (47% yield) of the title compound with a diastereomeric excess of 60%.

Workup

  1. customThe title compound was prepared
  2. customPurification by flash column chromatography (eluent DCM: methanol gradient)

Sources & evidence

ORD record
ord-641aced37a554c0ca6e799460938a332
Source dataset
uspto-grants-2011_06
Patent number
US07960395B2

Reaction notes

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