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

HRID 1694547Notes

Reaction equation

HRID 1694547 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%. Of this material 55 mg was further purified by preparative HPLC. The last eluting isomer was collected to yield 21 mg of the title compound.

Workup

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

Sources & evidence

ORD record
ord-dd564f6d6bd24c8692feb446c2775d99
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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